Tag: M.W=300-400

88784-33-2, A common heterocyclic compound, 88784-33-2, name is (S)-5-(Benzyloxy)-2-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid, molecular formula is C20H17NO6, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

a (1S-cis)-Octahydro-9-phthalimido-6,10-dioxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid, 1,1-dimethylethylester 5,6-Dihydro-1,3(2H,4H)-pyridazinedicarboxylic acid, 3-(1,1-dimethylethyl)-1-(phenylmethyl)ester [prepared as described by Adams et al., Synthetic Communications, 18(18), 2225-2231 (1988)] was reacted with (S)-2-phthalimidopentanedioic acid, 5-(phenylmethyl) ester according to the procedure described by Attwood et al.(J. Chem. Soc. Perkins Trans I, 1986, p. 1011-1019) affording (S)-2-[2-phthalimido-1,5-dioxo-5-(phenylmethoxy)pentyl]-5,6-dihydro-1,3(2H,4H)-pyridazinedicarboxylic acid, 3-(1,1-dimethylethyl)-1-(phenylmethyl) ester.

The synthetic route of 88784-33-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US5552397; (1996); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1168150-46-6, The chemical industry reduces the impact on the environment during synthesis 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

The chemical industry reduces the impact on the environment during synthesis (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 1168150-46-6

(3) Preparation of methyl (Z)-3-((1-(2-(dimethylamino) acetyl)indolin-5-ylamino)(phenyl)methylene)-2-oxoindoline-6-carboxylate and its hydrochloride1-(2-(dimethylamino) acetyl)-5-aminoindoline (0.082g, 0.3mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (0.086g, 0.28mmol) was added to MeOH (2ml). The resulting mixture was heated to 70 C and kept for 7 hours. After being cooled naturally, the mixture was filtered by suction. The filtrate was dried to produce a yellow solid (61mg) in a yield of 35.4%.Methanol (10ml) was added to a concentrated hydrochloric acid (1ml). The above crude product was added to the resulting solution. The mixture was stirred at room temperature for 2 hours, and filtered by suction. The filtrate was dried in vacuum to produce methyl (Z)-3-((1-(2-(dimethylamino) acetyl)indolin-5-ylamino)(phenyl)methylene)-2oxoindoline-6-carboxylate hydrochloride (68mg) as a yellow solid. Formula: C29H28N4O4; MW: 496.2; Mass Spectrum (m/e): 497.3 (M+1) 1H NMR (400MHz; hydrochloride, DMSO-d6, deltappm) ? 12.16 (s, 1H), 10.96 (s, 1H), 9.77 (br. s., 1H), 7.79 (d, J = 8.8 1H), 7.56 (m, 3H), 7.45 (m, 2H), 7.26 (s, 1H), 7.17(m, 1H), 6.88 (s, 1H), 6.74 (s, 1H), 5.81(d, J = 8.4, 1H), 4.25 (m, 2H), 3.96(m, 2H), 3.76 (s, 3H), 3.04 (m, 2H), 2.83 (m, 6H).

Statistics shows that 1168150-46-6 is playing an increasingly important role. we look forward to future research findings about (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate.

Reference:
Patent; KBP Biosciences Co., Ltd.; LO, Hoyin; WANG, Aichen; ZHANG, Qian; EP2930167; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

446292-07-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A compound having the structure of formula (I) (106.76 g, 270 mmol) was suspended in 4000 ml of anhydrous tetrahydrofuran(About 40ml / g), stir, gradually heated to 50 C, maintained at 50 C,A solution of triphosgene (80.2 g, 270 mmol) in tetrahydrofuran (268 ml) was added dropwise over 30 minutes,Heated to 64 C reflux, about 10 minutes after the clarification, about 1 hour and precipitation of solid, let cool to room temperature,The filter cake was washed with absolute ethanol (120 ml * 3 times) and air dried at 45 C to give 111.4 g of a compound having the structure of formula (II) in a yield of 97.9%

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SHENZHEN HYBIO PHARMACEUTICAL CO., LTD.; YUAN, HUIXING; XIAO, QING; LI, GUOTAO; MA, YAPING; YUAN, JIANCHENG; (21 pag.)CN104016975; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 1168150-46-6

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1168150-46-6.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem