Sodium hydride → 11-Ethyl-4-trifluoromethyl-2-methyl-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6(11H)-one
Reaction equation
Cl[C:2]1[C:7]([NH:8][C:9]([C:11]2[C:12]([NH:17][CH2:18][CH3:19])=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[C:6]([C:20]([F:23])([F:22])[F:21])[CH:5]=[C:4]([CH3:24])[N:3]=1.[H-].[Na+]>N1C=CC=CC=1>[CH2:18]([N:17]1[C:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:9](=[O:10])[NH:8][C:7]2[C:6]([C:20]([F:23])([F:22])[F:21])=[CH:5][C:4]([CH3:24])=[N:3][C:2]1=2)[CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A solution of 0.5 g of N-(2-chloro-6-methyl-4-trifluoromethyl-3-pyridinyl)-2-ethylamino-3pyridinecarboxamide in 3 ml of pyridine was added to 0.2 g of a 50% dispersion of sodium hydride in oil. The mixture was heated to 150° C. and then cooled and concentrated in vacuo. Water was added to the residue and the product was extracted with ethyl acetate, dried (magnesium sulfate), filtered, and concentrated. The product was purified by column chromatography over silica gel (methylene chloride, then methylene chloride/methanol). After concentrating in vacuo, the residue was crystallized from hexane to give 0.09 g of the title compound, m.p. 150°-151° C.
Workup
- temperaturecooled
- concentrationconcentrated in vacuo
- additionWater was added to the residue
- extractionthe product was extracted with ethyl acetate
- dry with materialdried (magnesium sulfate)
- filtrationfiltered
- concentrationconcentrated
- customThe product was purified by column chromatography over silica gel (methylene chloride
- concentrationAfter concentrating in vacuo
- customthe residue was crystallized from hexane
Sources & evidence
- ORD record
- ord-fb65b49f987f4ae2b0bd18991deb0d31
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05620974
Reaction notes
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