3-(Trifluoromethyl)benzoyl chloride → HCID 67360061, compound

HRID 1465021Notes

Reaction equation

HRID 1465021 reaction equation
[NH2:1][C:2]1[C:3]2[S:10][CH:9]=[C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:15]=3[CH3:21])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28]>C1COCC1.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]2[S:10][CH:9]=[C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH:20][C:27](=[O:28])[C:26]4[CH:30]=[CH:31][CH:32]=[C:24]([C:23]([F:22])([F:33])[F:34])[CH:25]=4)[CH:17]=[CH:16][C:15]=3[CH3:21])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 67327584HCID 67327584, compound

Product 1

HCID 67360061HCID 67360061, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Amino-N-(5-amino-2-methylphenyl)thieno[3,2-d]pyrimidine-7-carboxamide (30 mg, 0.1 mmol) was dissolved in THF (1 mL) and TEA (42 μL, 0.30 mmol) was added thereto. 3-(trifluoromethyl)benzoyl chloride (19 μL, 0.13 mmol) was added to reaction mixture at 0° C. and stirred at room temperature for 6 hours. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with brine. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure. The resulting mixture was purified by silica gel chromatography (3/97 MeOH/DCM) to obtain the title compound (35 mg, 74% yield).

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting mixture was purified by silica gel chromatography (3/97 MeOH/DCM)

Sources & evidence

ORD record
ord-41ec9e51ebbd4062914a659477c13e1b
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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