3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-N-(2-morpholinoethyl)benzamide

Base Information

• Chemical Name: 3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-N-(2-morpholinoethyl)benzamide
• CAS No.: 1350815-95-0
• Molecular Formula: C₂₅H₂₅ClN₆O₃
• Molecular Weight: 492.965

Synonyms:3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-N-(2-morpholinoethyl)benzamide

Chemical Property of 3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-N-(2-morpholinoethyl)benzamide

Chemical Property:

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Technology Process of 3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-N-(2-morpholinoethyl)benzamide

There total 7 articles about 3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-N-(2-morpholinoethyl)benzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 3-[(9-chloro-6-oxo-6,7-dihydro-5H-pyrimido[5,4-d][1]benzazepin-2-yl)amino]benzoic acid → 3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-N-(2-morpholinoethyl)benzamide (1350815-95-0)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jm2011172

Reference yield:

2-amino-4-chloro-benzoic acid methyl ester (5900-58-3) → 3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-N-(2-morpholinoethyl)benzamide (1350815-95-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 10 °C

2.2: 20 °C / pH 4

3.1: water / dimethyl sulfoxide / 150 °C / Cooling

3.2: 0 °C

4.1: tetrahydrofuran / 2 h / 60 °C / Inert atmosphere

5.1: potassium carbonate / ethanol / 90 °C

6.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

With dmap; potassium tert-butylate; water; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 2.1: Dieckmann reaction;

DOI:10.1021/jm2011172

Reference yield:

methyl N-(3-carbomethoxypropionyl)-4-chloroanthranilate (59868-48-3) → 3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-N-(2-morpholinoethyl)benzamide (1350815-95-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium tert-butylate / tetrahydrofuran / 10 °C

1.2: 20 °C / pH 4

2.1: water / dimethyl sulfoxide / 150 °C / Cooling

2.2: 0 °C

3.1: tetrahydrofuran / 2 h / 60 °C / Inert atmosphere

4.1: potassium carbonate / ethanol / 90 °C

5.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

With potassium tert-butylate; water; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Dieckmann reaction;

DOI:10.1021/jm2011172

upstream raw materials:

4-(2-AMINOETHYL)MORPHOLINE

2-amino-4-chloro-benzoic acid methyl ester

3-guanidino-benzoic acid nitric acid salt

8-chloro-4<(dimethylamino)methylidene>-3,4-dihydro-1H-1-benzazepine-2,5-dione

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