Benzoyl chloride → HCID 19979516, compound

HRID 1461833Notes

Reaction equation

HRID 1461833 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:26]4[C:21](=[CH:22][C:23]([F:27])=[CH:24][CH:25]=4)[NH:20][N:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[C:35]([Cl:43])(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CCOCC>[ClH:43].[C:35]([N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[C:18]([N:15]2[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][CH:8]([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:13][CH2:14]2)=[N:19]1)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 14823474HCID 14823474, compound

Product 1

HCID 19979516HCID 19979516, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-{4[4,4-bis(4-fluorophenyl)butyl]-1-piperazinyl}-6-fluoro-1H-indazole (3.7 g, 0.008 mol) of Example 36 and benzoyl chloride (18.2 g, 0.129 mol) was warmed on a steam bath under N2 for 2 hours. The reaction was cooled to room temperature and the only residue was diluted with ether. The product was isolated by vacuum filtration and the filter cake was washed well with ether affording 4.2 g of a solid. The product was recrystallized twice from ethanol to provide 2.7 g (50%) of 1-benzoyl-3-{4-[4,4-bis(4-fluorophenyl)butyl]-1-piperazinyl}-6-fluoro-1H-indazole hydrochloride, mp 236°-238° C.

Workup

  1. temperaturewas warmed on a steam bath under N2 for 2 hours
  2. customThe product was isolated by vacuum filtration
  3. washthe filter cake was washed well with ether affording 4.2 g of a solid
  4. customThe product was recrystallized twice from ethanol

Sources & evidence

ORD record
ord-b75c2738cce34789865f1f6b1178ae46
Source dataset
uspto-grants-1991_12
Patent number
US05077405

Reaction notes

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