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

HRID 1398122Notes

Reaction equation

HRID 1398122 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)([CH3:9])[C:6]([OH:8])=O.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[C:29]1[O:33][C:32]([CH3:34])=[N:31][CH:30]=1)[C:22]([NH:24][NH2:25])=[O:23].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C.O.[Cl-].[Na+].O>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)([CH3:9])[C:6]([NH:25][NH:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][C:28]([C:29]2[O:33][C:32]([CH3:34])=[N:31][CH:30]=2)=[C:19]([O:18][CH3:17])[CH:20]=1)=[O:8]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 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)benzohydrazideHCID 666087645-Chloro-2-(4-chlorophenyl)-2-methylpentanoic acid

Product 1

HCID 66608017N'-[5-chloro-2-(4-chlorophenyl)-2-methylpentanoyl]-3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazideYield 82.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 5-chloro-2-(4-chlorophenyl)-2-methylpentanoic acid (6.34 g), 3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide (5.0 g) and triethylamine (6.78 mL) in DMF (50 mL) was added HATU (9.23 g) at 0° C., and the mixture was stirred at room temperature for 14 hr. The reaction mixture was diluted with ethyl acetate (50 mL), water (150 mL) and saturated brine (50 mL), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine (4×50 mL), and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.19 g). 1H NMR (300 MHz, CDCl3) δ1.54-1.82 (2H, m), 1.66 (3H, s), 2.14-2.23 (2H, m), 2.54 (3H, s), 3.52 (2H, t, J=6.3 Hz), 3.90 (3H, s), 7.35-7.37 (6H, m), 7.48 (1H, s), 7.69 (1H, d, J=8.4 Hz), 7.95 (1H, d, J=4.2 Hz), 9.35 (1H, d, J=4.5 Hz).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine (4×50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dcede4f87ad244778c70eaed1d3ba49e
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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