Propyl mercaptan → 6-chloro-N-cyclohexyl-5-fluoro-2-(propylthio)nicotinamide

HRID 2424922Notes

Reaction equation

HRID 2424922 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([SH:14])[CH2:12][CH3:13].Cl[C:16]1[N:30]=[C:29]([Cl:31])[C:28]([F:32])=[CH:27][C:17]=1[C:18]([NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:19]>C1COCC1.CN(C=O)C>[Cl:31][C:29]1[C:28]([F:32])=[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:14][CH2:11][CH2:12][CH3:13])[N:30]=1

Participants

6

Reactant 3

HCID 7848Propyl mercaptanHCID 2724254Sodium bis(trimethylsilyl)amideHCID 598307712,6-dichloro-N-cyclohexyl-5-fluoronicotinamide

Product 1

HCID 598306576-chloro-N-cyclohexyl-5-fluoro-2-(propylthio)nicotinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of sodium bis(trimethylsilyl)amide (8.24 mL, 8.24 mmol) in THF (1M) was added to a stirred solution of 1-propanethiol (0.622 mL, 6.87 mmol) in DMF (30 mL) at 5° C., over a period of 3 minutes under air. The resulting suspension was stirred at 20° C. for 15 minutes. 2,6-dichloro-N-cyclohexyl-5-fluoronicotinamide (2.0 g, 6.87 mmol) in DMF (10 mL) was added at room temperature.

Sources & evidence

ORD record
ord-d66198d4be61478197809bb99f111c51
Source dataset
uspto-grants-2011_06
Patent number
US07964618B2

Reaction notes

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