1,4-Dioxane → N-(carboxymethyl)-2-[[3-(chloromethyl)-6-nitroindolin-1-yl]carbonyl]indole-6-carboxamide

HRID 1603050Notes

Reaction equation

HRID 1603050 reaction equation
C([O:5][C:6]([CH2:8][NH:9][C:10]([C:12]1[CH:20]=[C:19]2[C:15]([CH:16]=[C:17]([C:21]([N:23]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=4)[CH:25]([CH2:35][Cl:36])[CH2:24]3)=[O:22])[NH:18]2)=[CH:14][CH:13]=1)=[O:11])=[O:7])CCC.O1CCOCC1>Cl>[C:6]([CH2:8][NH:9][C:10]([C:12]1[CH:20]=[C:19]2[C:15]([CH:16]=[C:17]([C:21]([N:23]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=4)[CH:25]([CH2:35][Cl:36])[CH2:24]3)=[O:22])[NH:18]2)=[CH:14][CH:13]=1)=[O:11])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 19608784N-[(butoxycarbonyl)methyl]-2-[[3-(chloromethyl)-6-nitroindolin-1-yl)carbonyl]indole-6-carboxamide

Product 1

HCID 390670N-(carboxymethyl)-2-[[3-(chloromethyl)-6-nitroindolin-1-yl]carbonyl]indole-6-carboxamideYield 80%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of N-[(butoxycarbonyl)methyl]-2-[[3-(chloromethyl)-6-nitroindolin-1-yl]carbonyl)indole-6-carboxamide (70 mg, 0.14 mmol) in HCl-saturated dioxane (20 mL) was stirred at 20° C. for 2 h, most of the dioxane evaporated, and the residue triturated with hot EtOAc to give N-(carboxymethyl)-2-[[3-(chloromethyl)-6-nitroindolin-1-yl]carbonyl]indole-6-carboxamide as a pale yellow powder (50 mg, 80%), mp 281° C. (dec.). 1H NMR [(CD3)2SO] δ12.57 (br s, 1H, CO2H), 12.20 (d, J=1.3 Hz, 1H, indole NH), 8.99 (d, J=2.2 Hz, 1H, H-7), 8.84 (t, J=5.9 Hz, 1H, amide NH), 8.07 (s, 1H, H-3' or H-7'), 8.05 (dd, J=8.3, 2.2 Hz, 1H, H-5), 7.79 (d, J=8.4 Hz, 1H, H-4'), 7.75 (d, J=8.3 Hz, 1H, H-4), 7.61 (dd, J=8.4, 1.3 Hz, 1H, H-5'), 7.30 (d, J=1.9 Hz, 1H, H-3' or H-7'), 4.87 (t, J=10.1Hz, 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), 3.95 (d, J=5.8 Hz, 2H, CONHCH2). Anal. (C23H17ClN4O6) C, H, N.

Workup

  1. customevaporated
  2. customthe residue triturated with hot EtOAc

Sources & evidence

ORD record
ord-edd0590fe78f42f09497210de6dc432b
Source dataset
uspto-grants-1999_11
Patent number
US05985909

Reaction notes

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