4-Methoxy-3-(trifluoromethyl)benzoyl chloride → HCID 9956539, compound

HRID 2297625Notes

Reaction equation

HRID 2297625 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C:7]([CH3:19])([CH3:18])[N:8]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9]2)=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][C:23]=1[C:31]([F:34])([F:33])[F:32]>ClCCl.C(N(CC)CC)C>[CH3:18][C:7]1([CH3:19])[CH2:6][C:5]2[C:10](=[CH:11][C:2]([NH:1][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:22]([O:21][CH3:20])=[C:23]([C:31]([F:34])([F:32])[F:33])[CH:24]=3)=[CH:3][CH:4]=2)[CH2:9][N:8]1[C:12](=[O:17])[C:13]([F:16])([F:14])[F:15]

Participants

5

Reactant 2

HCID 27752984-Methoxy-3-(trifluoromethyl)benzoyl chlorideHCID 18382578HCID 18382578, compound

Product 1

HCID 9956539HCID 9956539, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 7-amino-3,3-dimethyl-1,2,3,4-tetrahydro-2-trifluoroacetylisoquinoline (408 mg; 1.5 mmol) in dichloromethane (20 ml) and triethylamine (0.6 ml) was treated with 4-methoxy-3-trifluoromethylbenzoyl chloride (358 mg; 1.5 mmol). The resultant solution was stirred at 25° C. for 1 h. The reaction mixture was then washed with water, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica, eluting with 1% methanol in dichloromethane, to give the title compound (442 mg).

Workup

  1. washThe reaction mixture was then washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica
  5. washeluting with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-93e238bbeb7d44b2bbcaaac41d7afe59
Source dataset
uspto-grants-2002_12
Patent number
US06492378B1

Reaction notes

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