Triethylamine → N'-[(3,4-difluorophenyl)acetyl]-3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide

HRID 71104Notes

Reaction equation

HRID 71104 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[C:13]1[O:17][C:16]([CH3:18])=[N:15][CH:14]=1)[C:6]([NH:8][NH2:9])=[O:7].[F:19][C:20]1[CH:21]=[C:22]([CH2:27][C:28](O)=[O:29])[CH:23]=[CH:24][C:25]=1[F:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[F:19][C:20]1[CH:21]=[C:22]([CH2:27][C:28]([NH:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][C:12]([C:13]3[O:17][C:16]([CH3:18])=[N:15][CH:14]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:29])[CH:23]=[CH:24][C:25]=1[F:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 69571(3,4-Difluorophenyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666079613-Methoxy-4-(2-methyloxazol-5-yl)benzohydrazide

Product 1

HCID 66607891N'-[(3,4-difluorophenyl)acetyl]-3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazideYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide (4.10 g), 3,4-difluorophenylacetic acid (3.15 g), HATU (7.57 g) and triethylamine (2.77 mL) in DMF (77 mL) was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the resultant precipitate was collected by filtration and washed with hexane and acetone to give the title compound (4.69 g).

Workup

  1. filtrationthe resultant precipitate was collected by filtration
  2. washwashed with hexane and acetone

Sources & evidence

ORD record
ord-58cabca568644da8b0e4737124422bf1
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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