Potassium Carbonate → (S)-methyl 2-(1-(5-(cyclohexylcarbamoyl)-3-fluoro-6-(propylthio)pyridin-2-yl)piperidin-3-yl)acetate

HRID 2424923Notes

Reaction equation

HRID 2424923 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3]1.Cl[C:14]1[C:28]([F:29])=[CH:27][C:17]([C:18]([NH:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:19])=[C:16]([S:30][CH2:31][CH2:32][CH3:33])[N:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)CCC>[CH:21]1([NH:20][C:18]([C:17]2[CH:27]=[C:28]([F:29])[C:14]([N:2]3[CH2:7][CH2:6][CH2:5][C@@H:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3]3)=[N:15][C:16]=2[S:30][CH2:31][CH2:32][CH3:33])=[O:19])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 45073966(S)-methyl 2-(piperidin-3-yl)acetate hydrochlorideHCID 598306576-chloro-N-cyclohexyl-5-fluoro-2-(propylthio)nicotinamide

Product 1

HCID 58000863(S)-methyl 2-(1-(5-(cyclohexylcarbamoyl)-3-fluoro-6-(propylthio)pyridin-2-yl)piperidin-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Conditions

Temperature
120 °C

Procedure

(S)-methyl 2-(piperidin-3-yl)acetate hydrochloride (263 mg, 1.36 mmol) was added to 6-chloro-N-cyclohexyl-5-fluoro-2-(propylthio)nicotinamide (500 mg, 1.51 mmol) and potassium carbonate (418 μl, 3.02 mmol) in butyronitrile (20 ml) at room temperature and under air. The resulting suspension was stirred at 120° C. for 80 hours.

Sources & evidence

ORD record
ord-b0f04bd511e647a0b763b18e8e5d0982
Source dataset
uspto-grants-2011_06
Patent number
US07964618B2

Reaction notes

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