4-Fluorobenzyl chloride → HCID 15037364, compound

HRID 1460528Notes

Reaction equation

[F:1][C:2]1[C:23]([F:24])=[CH:22][C:5]2[NH:6][C:7]([NH:9][CH:10]3[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][CH2:11]3)=[N:8][C:4]=2[CH:3]=1.Cl[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:1][C:2]1[C:23]([F:24])=[CH:22][C:5]2[N:6]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:7]([NH:9][CH:10]3[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][CH2:11]3)=[N:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 11 parts of ethyl 4-[[5,6-difluoro-1H-benzimidazol-2-yl]amino]hexahydro-1H-azepine-1-carboxylate, 7.2 parts of 1-(chloromethyl)-4-fluorobenzene, 3.2 parts of sodium carbonate and 90 parts of N,N-dimethylformamide was stirred and heated for 24 hours at 80° C. The reaction mixture was evaporated and the residue was taken up in water. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 6 parts (40.6%) of ethyl 4-[[5,6-difluoro-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]hexahydro-1H-azepine-1-carboxylate as a residue; (compound 35).

Workup

customThe reaction mixture was evaporated
extractionThe product was extracted with dichloromethane
customThe extract was dried
filtrationfiltered
customevaporated
customThe residue was purified by column chromatography over silica gel
customThe pure fractions were collected
customthe eluent was evaporated

Sources & evidence

ORD record: ord-d4f8d80536244e27b03c4691f2dbb875
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05071846

Reaction notes

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