Calcium Carbonate → HCID 66725396, compound

HRID 559816Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:38]=[CH:37][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14](=[O:36])[N:15]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[C:16]([CH3:25])=[C:17]([C:19]3[O:20][CH:21]=[C:22]([CH3:24])[N:23]=3)[CH:18]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[CH:40](C)C(=O)C.C([O-])([O-])=O.[Ca+2].CN1C(=O)CCC1>C(#N)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14](=[O:36])[N:15]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=3)[C:16]([CH3:25])=[C:17]([C:19]3[O:20][C:21]([CH3:40])=[C:22]([CH3:24])[N:23]=3)[CH:18]=2)=[O:12])=[CH:37][CH:38]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 140 °C

Procedure

6-Methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3,5-dicarboxylic acid 5-amide 4-methanesulfonyl-benzylamide (see Example 60, 0.05 g, 0.098 mmol), 3-bromo-2-butanone (0.020 g, 0.20 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, 140 ° C.) for 2 h. The reaction was stopped and the crude mixture was dissolved in acetonitrile (2 ml) and water (2 ml) and was purified directly on preparative HPLC, giving the title compound (0.007 g, 13%) as a slightly brownish solid after freeze-drying the pure fractions.

Workup

customdesigned for microwave synthesis
customThe vial was sealed
customwater (2 ml) and was purified directly on preparative HPLC

Sources & evidence

ORD record: ord-d40241082a9e44bfa8d546c278cd5551
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063073B2

Reaction notes

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