Ammonia → HCID 66725294, compound

HRID 559815Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:35]=[CH:34][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:16]([CH3:30])=[C:15]([C:31](O)=[O:32])[CH:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH3:36].Cl[CH2:38][C:39]([CH3:41])=O.C([O-])([O-])=O.[Ca+2]>CN1C(=O)CCC1>[CH3:1][S:2]([C:5]1[CH:35]=[CH:34][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:18](=[O:19])[N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:29])[F:28])[CH:21]=3)[C:16]([CH3:30])=[C:15]([C:31]3[O:32][CH:38]=[C:39]([CH3:41])[N:36]=3)[CH:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 155 °C

Procedure

6-Methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3,5-dicarboxylic acid 5-amide 4-methanesulfonyl-benzylamide [prepared from the acid chloride of 5-(4-methanesulfonyl-benzylcarbamoyl)-2-methyl-6-oxo-1-(3-trifluoromethyl-phenyl)-1,6-dihydro-pyridine-3-carboxylic acid [described in Example 14 (b)] and ammonia] (0.05 g, 0.098 mmol), 1-chloroacetone (0.025 g, 0.27 mmol), CaCO3 (0.015 g, 0.15 mmol), NMP (1.5 ml) and a magnetic stirrer bar were placed in a tube designed for microwave synthesis. The vial was sealed and the mixture was heated in a CEM Discover Microwave apparatus (100 W, 155° C.) for 60 minutes, giving complete conversion of the amide according to LC-MS. The crude mixture was dissolved in acetonitrile (2 ml) and water (2 ml) and was purified directly on preparative HPLC giving the title compound (0.006 g, 11%) as a solid after freeze-drying the pure fractions.

Workup

customwere placed in a tube
customdesigned for microwave synthesis
customThe vial was sealed

Sources & evidence

ORD record: ord-592136375f234754af79ca49139c315c
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063073B2

Reaction notes

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