4-Fluorobenzyl chloride → HCID 15037364, compound

HRID 704721Notes

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-02caebf4660a49ea8be6da1b83f2cf7c
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04988689

Reaction notes

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