4-Fluoroaniline → HCID 178522148, compound

HRID 1910135Notes

Reaction equation

[NH2:1][C:2]1[C:7]2[NH:8][C:9]([NH:11][C:12]([C:14]3[N:15]=[CH:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:13])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.N1([C:29]([N:31]2[CH:35]=[CH:34]N=C2)=[O:30])C=CN=C1.[F:36][C:37]1[CH:42]=CC(N)=[CH:39][CH:38]=1>CN(C=O)C>[F:36][C:37]1[CH:42]=[CH:34][C:35]([NH:31][C:29](=[O:30])[NH:1][C:2]2[C:7]3[NH:8][C:9]([NH:11][C:12]([C:14]4[N:15]=[CH:16][C:17]5[C:22]([CH:23]=4)=[CH:21][CH:20]=[CH:19][CH:18]=5)=[O:13])=[N:10][C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 30 mg (0.1 mmol) of above isoquinoline-3-carboxylic acid (7-amino-1H-benzoimidazol-2-yl)-amide in dry DMF (1 mL) was added 24 mg (0.15 mmol) of di-imidazol-1-yl-methanone in one portion. The mixture was heated at 50° C. for 30 min. After cooling to room temperature, 16 mg (0.15 mmol) of 4-fluoro-phenylamine was added to the reaction. The reaction mixture was stirred at 45° C. for 45 min. After cooling to room temperature, the organic solvent was removed under reduced pressure, and the residue was purified by column chromatography eluting with DCM/methanol (v/v=10:0.5 to 10:1) to provide 17 mg (39%) of isoquinoline-3-carboxylic acid {7-[3-(4-fluoro-phenyl)-ureido]-1H-benzoimidazol-2-yl}-amide. LCMS: 441 (M+1)+.

Workup

temperatureAfter cooling to room temperature
temperatureAfter cooling to room temperature
customthe organic solvent was removed under reduced pressure
customthe residue was purified by column chromatography
washeluting with DCM/methanol (v/v=10:0.5 to 10:1)

Sources & evidence

ORD record: ord-9c154db35a4f417b9b1cbc6c59423ff2
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598353B2

Reaction notes

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