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

HRID 1748343ノート

反応式

HRID 1748343 の反応式
[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

参加物

7

反応物 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 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-65e863b81c8d473189a3d06aede1fbdb
出典データセット
uspto-grants-2015_10
特許番号
US09150577B2

反応ノート

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