Acetyl chloride → HCID 67314334, compound

HRID 1011985Notes

Reaction equation

HRID 1011985 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:25][NH2:26])=[N:8][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=2)[C:10]=1[CH:11]1[CH2:13][CH2:12]1)=[O:5])[CH3:2].CCN(C(C)C)C(C)C.[C:36](Cl)(=[O:38])[CH3:37]>C1COCC1.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:25][NH:26][C:36](=[O:38])[CH3:37])=[N:8][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:23])([F:22])[F:24])[CH:15]=2)[C:10]=1[CH:11]1[CH2:12][CH2:13]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67314428HCID 67314428, compound

Product 1

HCID 67314334HCID 67314334, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-aminomethyl-5-cyclopropyl-1-(3-trifluoromethoxy-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester (46 mg, 0.12 mmol) and iPr2NEt (0.06 ml, 0.37 mmol) in 0.5 ml THF under ice cooling was treated with acetylchloride (0.011 ml, 0.15 mmol). The yellow suspension was stirred 2 h at 0° C., then diluted with EtOAc and washed with water and brine. The aqueous phases were extracted with EtOAc. The organic layers were dried over magnesium sulfate, evaporated and chromatographed (amino-phase silica gel, EtOAc) to give the title compound as a yellow oil (37 mg, 72%). MS: 412.3 (MH+).

Workup

  1. washwashed with water and brine
  2. extractionThe aqueous phases were extracted with EtOAc
  3. dry with materialThe organic layers were dried over magnesium sulfate
  4. customevaporated
  5. customchromatographed (amino-phase silica gel, EtOAc)

Sources & evidence

ORD record
ord-6bfecf4108ea417e829644b67f1bb280
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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