Tetrahydrofuran → N-[2-[1-(chloromethyl)-5-nitro-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-5-yl]acetamide

HRID 366808

反応式

HRID 366808 の反応式
C(O[C:6]([N:8]1[C:16]2[CH:15]=[C:14]([N+:17]([O-:19])=[O:18])[C:13]3[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=3[C:11]=2[CH:10]([CH2:24][Cl:25])[CH2:9]1)=O)(C)(C)C.[C:26]([NH:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34]([C:39]([OH:41])=O)=[CH:33]2)(=[O:28])[CH3:27].C1COCC1>CC(N(C)C)=O>[CH3:27][CH2:26][N:29]=[C:30]=[N:17][CH2:14][CH2:15][CH2:16][N:8]([CH3:6])[CH3:9].[ClH:25].[C:26]([NH:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34]([C:39]([N:8]1[C:16]3[CH:15]=[C:14]([N+:17]([O-:19])=[O:18])[C:13]4[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=4[C:11]=3[CH:10]([CH2:24][Cl:25])[CH2:9]1)=[O:41])=[CH:33]2)(=[O:28])[CH3:27]

参加物

6

反応物 3

HCID 8028TetrahydrofuranHCID 107751705-acetamido-1H-indole-2-carboxylic AcidHCID 153804133-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole

生成物 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4365483N-[2-[1-(chloromethyl)-5-nitro-1,2-dihydrobenzo[e]indole-3-carbonyl]-1H-indol-5-yl]acetamide収率 79%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

Deprotection of 13 (300 mg, 0.83 mmol) as in Example C, and treatment with 5-acetylaminoindole-2-carboxylic acid [M. A. Warpehoski et al., J. Med. Chem. 31, 1988, 590-603] (181 mg, 0.83 mmol) and EDCI.HCl (397 mg, 2.07 mmol) in DMA (3 mL) gave 14c (310 mg, 79%), mp (THF) 252-253° C. 1H NMR [(CD3)2SO] δ 11.77 (d, J=1.2 Hz, 1 H, indole NH), 9.86 (s, 1 H, NHCO), 9.16 (s, 1 H, H-4), 8.35 (dd, J=7.1, 2.6 Hz, 1 H, H-6), 8.24 (dd, J=6.8, 2.5 Hz, 1 H, H-9), 8.10 (d, J=1.3 Hz, H-4'), 7.79-7.70 (m, 2 H, H-7,8), 7.43 (d, J=8.8 Hz, 1 H, H-7'), 7.35 (dd, J=8.8, 1.8 Hz, 1 H, H-6'), 7.27 (d, J=1.8 Hz, 1 H, H-3'), 4.94 (t, J=10.2 Hz, 1 H, H-2), 4.71 (dd, J=11.0, 2.3 Hz, 1 H, H-2), 4.66-4.58 (m, 1 H, H-1), 4.13 (d, J=4.3 Hz, 2 H, CH2Cl), 2.06 (s, 3 H, COCH3).

出典と根拠

ORDレコード
ord-502d11aa9fa94273a604bbd5ecb60bef
出典データセット
uspto-grants-2000_10
特許番号
US06130237

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