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

HRID 1748343Notes

Reaction equation

HRID 1748343 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.F[B-](F)(F)F.N1(OC(=[N+](C)C)N(C)C)C2C=CC=CC=2N=N1.[Cl:41][C:42]1[CH:43]=[C:44]([NH2:48])[CH:45]=[CH:46][CH:47]=1.C(N(CC)CC)C>CN(C=O)C.O>[Cl:41][C:42]1[CH:43]=[C:44]([NH:48][C:16]([C:13]2[CH:12]=[CH:11][C:10]3[CH:9]=[C:8]4[C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][N:7]4[C:15]=3[CH:14]=2)=[O:18])[CH:45]=[CH:46][CH:47]=1

Participants

7

Reactant 4

HCID 79323-ChloroanilineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 672357061-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid2×

Product 1

HCID 57401079N-(3-chlorophenyl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamideYield 56.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 49 mg, 0.2 mmol) in DMF (1 mL) is added [(benzotriazol-1-yloxy)-dimethylamino-methylene]dimethyl-ammonium tetrafluoroborate (TBTU) (77 mg, 0.24 mmol) and the reaction is stirred for 10 minutes. The reaction is then treated with 3-chloro-phenylamine (28 mg, 0.22 mmol) followed by triethylamine (0.10 mL, 0.7 mmol) and is stirred for 16 h. The reaction is poured into water (20 mL) and the resulting solid is filtered. The solid is dried, suspended in MTBE (20 mL) and filtered again to afford the title compound (40 mg, 56%) as an off-white solid.

Workup

  1. stirringis stirred for 16 h
  2. filtrationthe resulting solid is filtered
  3. customThe solid is dried
  4. filtrationfiltered again

Sources & evidence

ORD record
ord-65e863b81c8d473189a3d06aede1fbdb
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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