Acetyl chloride → N-((1-((6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methyl)acetamide

HRID 1091697Notes

Reaction equation

HRID 1091697 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([C:20]([F:23])([F:22])[F:21])=[N:5][N:6]([CH2:8][C:9]2[NH:10][C:11](=[O:19])[C:12]3[CH:17]=[C:16]([CH3:18])[S:15][C:13]=3[N:14]=2)[CH:7]=1.CCN(C(C)C)C(C)C.[C:33](Cl)(=[O:35])[CH3:34]>C(Cl)Cl>[CH3:18][C:16]1[S:15][C:13]2[N:14]=[C:9]([CH2:8][N:6]3[CH:7]=[C:3]([CH2:2][NH:1][C:33](=[O:35])[CH3:34])[C:4]([C:20]([F:22])([F:21])[F:23])=[N:5]3)[NH:10][C:11](=[O:19])[C:12]=2[CH:17]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 665917222-((4-(aminomethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 66591725N-((1-((6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)methyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-((4-(aminomethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one (0.087 mmol, 30 mg) and DIPEA (0.175 mmol, 0.029 ml, 22.59 mg) in DCM (1 mL) was added acetyl chloride (0.175 mmol, 0.012 ml, 13.72 mg). The whole was stirred at room temperature overnight before the reaction mixture was concentrated under reduced pressure and the residue purified by reverse phase HPLC to give a white solid (8.7 mg, 23 mmol. 25.8%)

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customthe residue purified by reverse phase HPLC
  3. customto give a white solid (8.7 mg, 23 mmol. 25.8%)

Sources & evidence

ORD record
ord-3c82303c57a14f9396076620b7acc072
Source dataset
uspto-grants-2012_03
Patent number
US08129397B2

Reaction notes

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