N-Methylacetamide → HCID 66725500, compound

HRID 559799Notes

Reaction equation

HRID 559799 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][NH:7][C:8](=O)[CH3:9].[CH3:11][S:12]([C:15]1[CH:46]=[CH:45][C:18]([CH2:19][NH:20][C:21]([C:23]2[C:24](=[O:44])[N:25]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=3)[C:26]([CH3:33])=[C:27]([C:29]([NH:31][NH2:32])=O)[CH:28]=2)=[O:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH3:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][NH:20][C:21]([C:23]2[C:24](=[O:44])[N:25]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:41])[F:42])[CH:35]=3)[C:26]([CH3:33])=[C:27]([C:29]3[N:7]([CH3:6])[C:8]([CH3:9])=[N:32][N:31]=3)[CH:28]=2)=[O:22])=[CH:45][CH:46]=1)(=[O:14])=[O:13]

Participants

6

Reactant 3

HCID 6582N-MethylacetamideHCID 24813Phosphorus oxychlorideHCID 66725214HCID 66725214, compound

Product 1

HCID 66725500HCID 66725500, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of POCl3 (0.030 g, 0.2 mmol) in CHCl3 (1 ml) and pyridine (1 ml) was added to N-methylacetamide (0.015 g, 0.2 mmol) and the mixture was cooled in an ice-water bath and stirred for 90 minutes. To this solution was added a solution of 5-hydrazinocarbonyl-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide (Example 38 (a), 0.040 g, 0.076 mmol) in CHCl3 (2 ml) and the mixture was stirred overnight at room temperature. Purification by preparative HPLC gave the linear intermediate (0.020 g). This material was suspended in EtOAc (2 ml) and was heated (90° C.) with stirring for 4 h, giving rise to a mixture of three components. This mixture was purified on preparative HPLC giving the title compound (0.003 g, 7%) after freeze-drying the pure fractions.

Workup

  1. temperaturethe mixture was cooled in an ice-water bath
  2. stirringthe mixture was stirred overnight at room temperature
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-03ca21c56b004ceb8fabaee68886591c
Source dataset
uspto-grants-2011_11
Patent number
US08063073B2

Reaction notes

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