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