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

HRID 1748343노트

반응식

HRID 1748343 반응식
[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

참가 물질

7

반응물 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 acid2회

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-65e863b81c8d473189a3d06aede1fbdb
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150577B2

반응 노트

불러오는 중…