Triethylamine → HCID 178509428, compound

HRID 460722Notes

Reaction equation

HRID 460722 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][C:17]3[N:18]([N:28]=[C:29]([C:31]([NH2:33])=O)[CH:30]=3)[C:19](=[O:27])[C:20]=2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[NH:16][C:17]3[N:18]([N:28]=[C:29]([C:31]#[N:33])[CH:30]=3)[C:19](=[O:27])[C:20]=2[CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 178513505HCID 178513505, compound

Product 1

HCID 178509428HCID 178509428, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 22 mg (0.05 mmol) of 5-(4-benzyloxy-phenyl)-6-cyclohexyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid amide in 1 mL of dichloromethane (DCM) was added 0.04 mL (0.3 mmol) of triethylamine (Et3N), and the resulting mixture was cooled in an ice bath. Then 0.021 mL (0.15 mmol) of trifluoroacetic anhydride ((CF3CO)2O) was added during which time the mixture became homogeneous, and was stirred for 2.5 h. The reaction mixture was quenched by the addition of water, and concentrated to a residue which was purified via reverse-phase chromatography to afford (after lyophilization) 3 mg (14% yield) of desired 5-(4-benzyloxy-phenyl)-6-cyclohexyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carbonitrile as indicated by LC-MS calcd for C26H24N4O2 [M++H]+: 425.19, found: 425.2.

Workup

  1. temperaturethe resulting mixture was cooled in an ice bath
  2. customThe reaction mixture was quenched by the addition of water
  3. concentrationconcentrated to a residue which
  4. customwas purified via reverse-phase chromatography

Sources & evidence

ORD record
ord-ad6ae84c2c0c4d3697fb8c5ce9c9e148
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Reaction notes

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