Tetrahydrothiopyran-4-one → N-(Tetrahydrothiopyran-4-yl)-4-trifluoromethylnicotinamide

HRID 2055589Notes

Reaction equation

HRID 2055589 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.S1CCC(=O)CC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:21][C:22]([F:33])([F:32])[C:23]1[C:28]([C:29](Cl)=[O:30])=[CH:27][N:26]=[CH:25][CH:24]=1>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[S:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:29](=[O:30])[C:28]2[C:23]([C:22]([F:33])([F:21])[F:32])=[CH:24][CH:25]=[N:26][CH:27]=2)[CH2:3][CH2:4]1

Participants

8

Reactant 4

HCID 66173Tetrahydrothiopyran-4-oneHCID 418807Tetrahydrothiopyran-4-ylamineHCID 117904654-Trifluoromethylnicotinoyl chlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 11680848N-(Tetrahydrothiopyran-4-yl)-4-trifluoromethylnicotinamideYield 51.3%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Analogously to Example A, equimolar amounts of 4-aminotetrahydrothiopyran (prepared from tetrahydrothiopyran-4-one via the corresponding oxime and subsequent reduction with lithium aluminum hydride in tetrahydrofuran) and 4-trifluoromethylnicotinoyl chloride were reacted in the presence of triethylamine. This gave, after silica gel chromatography (ethyl acetate), the amide as a colorless solid of melting point 161-163° C. (Yield 51.3% of theory).

Sources & evidence

ORD record
ord-6274030001d644ee81a1b28d2f477363
Source dataset
uspto-grants-2008_02
Patent number
US07332509B2

Reaction notes

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