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

HRID 1398134Notes

Reaction equation

HRID 1398134 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-29e8ceb103954c80b1398f330265441e
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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