Benzoyl chloride → HCID 19979516, compound

HRID 1031521Notes

Reaction equation

HRID 1031521 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, compound

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
  5. customto 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.

Sources & evidence

ORD record
ord-1d720873a12e44b599e167e1fad02e21
Source dataset
uspto-grants-1990_09
Patent number
US04954503

Reaction notes

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