Diisopropylethylamine → 1-Methyl-N'-[4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-carbohydrazide

HRID 238373

Reaction equation

HRID 238373 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=1.[CH3:15][N:16]1[C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=[N:17]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O.CN(C)C=O>[CH3:15][N:16]1[C:20]([C:21]([NH:10][NH:9][C:7](=[O:8])[C:6]2[CH:11]=[CH:12][C:3]([C:2]([F:13])([F:14])[F:1])=[CH:4][CH:5]=2)=[O:22])=[CH:19][CH:18]=[N:17]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5206624-(Trifluoromethyl)benzohydrazideHCID 6431581-methyl-1H-pyrazole-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 866848721-Methyl-N'-[4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-carbohydrazideYield 80.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(Trifluoromethyl)benzohydrazide (583 mg) was added to a dimethylformamide (6.8 mL) solution that contained 1-methyl-1H-pyrazol-5-carboxylic acid (300 mg), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.09 g) and diisopropylethylamine (830 μL) at a room temperature, and the obtained solution was then stirred for 19 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The obtained solid was washed with ethyl acetate/hexane (1:1), so as to obtain the title compound (598 mg) in the form of a colorless solid. The filtrate was concentrated under a reduced pressure, and the residue was then purified by column chromatography (silica gel cartridge, chloroform:methanol=10:0 to 9:1), so as to further obtain the title compound (109 mg) in the form of a colorless solid.

Workup

  1. customat a room temperature
  2. extractionthe obtained mixture was then extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated saline, and was then dried over anhydrous magnesium sulfate
  5. concentrationfollowed by vacuum concentration
  6. washThe obtained solid was washed with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-d2a92c3296354ea2ae6d38e2d2c47bbf
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Linked notes

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