6-(Trifluoromethyl)benzo[b]thiophene-2-carbonyl chloride → 2,2,2-Trifluoro-1-(4-(1-(6-(trifluoromethyl)benzo[b]thiophene-2-carbonyl)azetidin-3-yl)piperazin-1-yl)ethanone

HRID 1961373Notes

Reaction equation

HRID 1961373 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11](Cl)=[O:12])[S:8][C:7]=2[CH:14]=1.[NH:17]1[CH2:20][CH:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH2:23][CH2:22]2)[CH2:18]1>C(Cl)Cl>[F:31][C:28]([F:29])([F:30])[C:27]([N:24]1[CH2:23][CH2:22][N:21]([CH:19]2[CH2:20][N:17]([C:11]([C:9]3[S:8][C:7]4[CH:14]=[C:3]([C:2]([F:16])([F:15])[F:1])[CH:4]=[CH:5][C:6]=4[CH:10]=3)=[O:12])[CH2:18]2)[CH2:26][CH2:25]1)=[O:32]

Participants

4

Reactant 2

HCID 577187896-(Trifluoromethyl)benzo[b]thiophene-2-carbonyl chlorideHCID 596256781-(4-Azetidin-3-yl-piperazin-1-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 866492442,2,2-Trifluoro-1-(4-(1-(6-(trifluoromethyl)benzo[b]thiophene-2-carbonyl)azetidin-3-yl)piperazin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-(trifluoromethyl)benzo[b]thiophene-2-carbonyl chloride (2.03 mmol, 537 mg) in CH2Cl2 (5 mL) was added to a solution of 1-(4-azetidin-3-yl-piperazin-1-yl)-2,2,2-trifluoro-ethanone (2.26 mmol, 700 mg) and TEA in CH2Cl2 (15 mL) at 0° C. The resulting mixture was allowed to warm to room temperature and was stirred for 2 h. Following workup and extraction, the residue was purified by flash column chromatography (silica gel, 3% methanol/CH2Cl2) to yield 2,2,2-trifluoro-1-(4-(1-(6-(trifluoromethyl)benzo[b]thiophene-2-carbonyl)azetidin-3-yl)piperazin-1-yl)ethanone.

Workup

  1. extractionworkup and extraction
  2. customthe residue was purified by flash column chromatography (silica gel, 3% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-d967302ba5fa426cb01cd331a617b234
Source dataset
uspto-grants-2013_04
Patent number
US08415341B2

Reaction notes

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