Pyridine → N-(2-carbamoylphenyl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

HRID 1748350Notes

Reaction equation

HRID 1748350 reaction equation
[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([OH:18])=O)=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.ClC(N(C)C)=C(C)C.[NH2:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH2:32])=[O:31].N1C=CC=CC=1>C(Cl)Cl.O>[C:30]([C:29]1[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=1[NH:27][C:16]([C:13]1[CH:12]=[CH:11][C:10]2[CH:9]=[C:8]3[C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][N:7]3[C:15]=2[CH:14]=1)=[O:18])(=[O:31])[NH2:32]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6942AnthranilamideHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 672357061-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid2×

Product 1

HCID 57392346N-(2-carbamoylphenyl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamideYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 100 mg, 0.41 mmol) in CH2Cl2 (1.5 mL) is added 1-chloro-N,N,2-trimethylpropenylamine (0.20 mL, 1.43 mmol). The reaction mixture is stirred for 5 h. 2-Aminobenzamide (200 mg, 1.47 mmol) and pyridine (0.12 mL, 1.48 mmol) are added and the reaction mixture is stirred for another 16 h at room temperature. Water (55 mL) is added and the resulting white solid is collected by filtration and purified by flash column chromatography using methanol in CH2Cl2 to afford the title compound (40 mg, 27%). LCMS (ESMS): m/z 363.61 (M+H+).

Workup

  1. stirringthe reaction mixture is stirred for another 16 h at room temperature
  2. filtrationthe resulting white solid is collected by filtration
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-4d0d532378d341f5a587ee0f4b223950
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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