1-(Isocyanatomethyl)-3-methoxybenzene → Tert-butyl-3-amino-5-[3-(3-methoxybenzyl)ureido]indazole-1-carboxylate

HRID 222380Notes

Reaction equation

HRID 222380 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:3]=1.[N:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1)=[C:20]=[O:21]>ClCCl>[C:15]([O:14][C:12]([N:4]1[C:5]2[C:10](=[CH:9][C:8]([NH:11][C:20]([NH:19][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=3)=[O:21])=[CH:7][CH:6]=2)[C:2]([NH2:1])=[N:3]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 36446341-(Isocyanatomethyl)-3-methoxybenzeneHCID 23571038tert-butyl 3,5-diamino-1H-indazole-1-carboxylate

Product 1

HCID 44249368Tert-butyl-3-amino-5-[3-(3-methoxybenzyl)ureido]indazole-1-carboxylateYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.1 3.3 g of tert-butyl 3,5-diaminoindazole-1-carboxylate (13.3 mmol) and 2.0 g of 1-isocyanatomethyl-3-methoxybenzene (12.3 mmol) are stirred at RT for 24 hours in 40 ml of dichloromethane. The reaction mixture is washed with water, the organic phase is separated off, dried and evaporated. Purification of the residue by column chromatography (eluent ethyl acetate) gives 3.5 g of tert-butyl-3-amino-5-[3-(3-methoxybenzyl)ureido]indazole-1-carboxylate (64%); MS-FAB (M+H+)=412.

Workup

  1. washThe reaction mixture is washed with water
  2. customthe organic phase is separated off
  3. customdried
  4. customevaporated
  5. customPurification of the residue by column chromatography (eluent ethyl acetate)

Sources & evidence

ORD record
ord-758fd5e5e21746559eff4cc065bdf9ba
Source dataset
uspto-grants-2012_06
Patent number
US08207210B2

Reaction notes

Loading…