3-Fluorobenzyl isocyanate → Tert-butyl 3-tert-butoxycarbonylamino-6-ethoxy-7-fluoro-5-[3-(3-fluorobenzyl)ureido]indazole-1-carboxylate

HRID 222383Notes

Reaction equation

HRID 222383 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]=[C:10]=[O:11])[CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([F:25])[C:21]=1[O:22][CH2:23][CH3:24])[N:18]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[N:17]=[C:16]2[NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>ClCCl>[C:37]([O:36][C:34]([NH:33][C:16]1[C:15]2[C:19](=[C:20]([F:25])[C:21]([O:22][CH2:23][CH3:24])=[C:13]([NH:12][C:10]([NH:9][CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[O:11])[CH:14]=2)[N:18]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[N:17]=1)=[O:35])([CH3:40])([CH3:38])[CH3:39]

Participants

4

Reactant 2

HCID 6434993-Fluorobenzyl isocyanateHCID 57908840Tert-butyl 5-amino-3-tert-butoxycarbonylamino-6-ethoxy-7-fluoroindazole-1-carboxylate

Product 1

HCID 57908848Tert-butyl 3-tert-butoxycarbonylamino-6-ethoxy-7-fluoro-5-[3-(3-fluorobenzyl)ureido]indazole-1-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.3 120 mg of 1-fluoro-3-isocyanatomethylbenzene (0.79 mmol) are added to 270 mg of tert-butyl 5-amino-3-tert-butoxycarbonylamino-6-ethoxy-7-fluoroindazole-1-carboxylate (0.66 mmol), dissolved in 10 ml of dichloromethane, and the mixture is stirred at RT for 24 hours. The reaction solution is evaporated, and the residue is purified by column chromatography on silica gel (eluent: 100% heptane->60% heptane/40% ethyl acetate), giving 250 mg of tert-butyl 3-tert-butoxycarbonylamino-6-ethoxy-7-fluoro-5-[3-(3-fluorobenzyl)ureido]indazole-1-carboxylate (68%), MS-FAB (M+H+)=562.

Workup

  1. customThe reaction solution is evaporated
  2. customthe residue is purified by column chromatography on silica gel (eluent: 100% heptane->60% heptane/40% ethyl acetate)

Sources & evidence

ORD record
ord-e9a4e0d7d1814a35b03ef02ee24b960c
Source dataset
uspto-grants-2012_06
Patent number
US08207210B2

Reaction notes

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