Dimethylformamide → 1-(2,6-difluoro-phenyl)-3-[3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-urea

HRID 1012147Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:17]([O:18][CH3:19])=[CH:16][C:6]2[NH:7][C:8]([C:10]3[C:14]([NH2:15])=[CH:13][NH:12][N:11]=3)=[N:9][C:5]=2[CH:4]=1.[F:20][C:21]1C=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1N=C=O.CCN(CC)CC.[CH3:38][N:39]([CH:41]=[O:42])C>CCO>[F:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([F:27])[C:38]=1[NH:39][C:41]([NH:15][C:14]1[C:10]([C:8]2[NH:7][C:6]3[CH:16]=[C:17]([O:18][CH3:19])[C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:9]=2)=[N:11][NH:12][CH:13]=1)=[O:42]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (50 mg, 0.19 mmol), 2,4 difluorophenyl isocyanate (31.4 mg, 0.20 mmol) and Et3N (0.027 ml) suspended in a mixture of DMF and EtOH (5 ml) was stirred at 70° C. for 1 h and then reduced in vacuo. The residue was purified by prep HPLC to give 1-(2,6-difluoro-phenyl)-3-[3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-urea as a white solid (11 mg) (LC/MS: Rt 2.10, [M+H]+ 415).

Workup

customThe residue was purified by prep HPLC

Sources & evidence

ORD record: ord-7c25ef382305494c9914691cf69dc47d
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977477B2

Reaction notes

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