1-(t-Butoxycarbonyl)-3-(chloromethyl)-6-nitroindoline → N-[(butoxycarbonyl)methyl]-2-[[3-(chloromethyl)-6-nitroindolin-1-yl)carbonyl]indole-6-carboxamide

HRID 1603049Notes

Reaction equation

HRID 1603049 reaction equation
C(O[C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[CH:10]([CH2:20][Cl:21])[CH2:9]1)=[O:7])(C)(C)C.[CH2:22]([O:26][C:27]([CH2:29][NH:30][C:31]([C:33]1[CH:41]=[C:40]2[C:36]([CH:37]=[C:38](C(O)=O)[NH:39]2)=[CH:35][CH:34]=1)=[O:32])=[O:28])[CH2:23][CH2:24][CH3:25]>>[CH2:22]([O:26][C:27]([CH2:29][NH:30][C:31]([C:33]1[CH:41]=[C:40]2[C:36]([CH:37]=[C:38]([C:6]([N:8]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=4)[CH:10]([CH2:20][Cl:21])[CH2:9]3)=[O:7])[NH:39]2)=[CH:35][CH:34]=1)=[O:32])=[O:28])[CH2:23][CH2:24][CH3:25]

Participants

3

Reactant 2

HCID 108289531-(t-Butoxycarbonyl)-3-(chloromethyl)-6-nitroindolineHCID 19608774N-[(butoxycarbonyl)methyl]-2-carboxyindole-6-carboxamide

Product 1

HCID 19608784N-[(butoxycarbonyl)methyl]-2-[[3-(chloromethyl)-6-nitroindolin-1-yl)carbonyl]indole-6-carboxamideYield 69%

Procedure

1-(t-Butoxycarbonyl)-3-(chloromethyl)-6-nitroindoline was coupled with N-[(butoxycarbonyl)methyl]-2-carboxyindole-6-carboxamide by the method described above and the product recrystallised from EtOAc to give with N-[(butoxycarbonyl)methyl]-2-[[3-(chloromethyl)-6-nitroindolin-1-yl)carbonyl]indole-6-carboxamide as a yellow solid (69%), mp 286° C. (dec.). 1H NMR [(CD3)2SO] δ12.20 (d, J=1.5 Hz, 1H, indole NH), 8.99 (d, J=2.2 Hz, 1H, H-7), 8.50 (t, J=6.0 Hz, 1H, amide NH), 8.06 (s, 1H, H-3' or H-7'), 8.05 (dd, J=8.2, 2.2 Hz, 1H, H-5), 7.78 (d, J=8.5 Hz, 1H, H-4'), 7.75 (d, J=8.2 Hz, 1H, H-4), 7.60 (dd, J=8.5, 1.4 Hz, 1H, H-5'), 7.30 (d, J=1.6 Hz, 1H, H-3' or H-7'), 4.87 (t, J=10.1 Hz, 1H, H-2), 4.51 (dd, J=10.7, 5.2 Hz, 1H, H-2), 4.19-4.08 (m, 3H, H-3 and CH2Cl), 3.92 (d, J=5.9 Hz, 2H, CONHCH2), 1.44 (s, 9H, t-Bu); 13C NMR δ169.1 (CO2 tBu), 167.1 (CONH), 160.4 (CON), 147.6, 144.6, 140.0, 135.7, 132.0, 130.0, 129.2 (C-6,8,9,2',6',8',9'), 125.5, 121.7, 119.4, 118.9, 112.2, 111.2, 106.1 (C-4,5,7,3',4',5',7'), 80.5 (OCMe3), 54.0 (C-2), 47.0 (CH2Cl), 42.0 (C-3), 41.9 (CH2CO2 tBu), 27.7 (t-Bu). Anal. (C25H25ClN4O6) C, H, N.

Workup

  1. customrecrystallised from EtOAc

Sources & evidence

ORD record
ord-86c0584085a8488c8ff6d8c2cf5a0f82
Source dataset
uspto-grants-1999_11
Patent number
US05985909

Reaction notes

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