Sodium Carbonate → 6-chloro-N-cyclohexyl-2-(cyclopentylthio)nicotinamide

HRID 1187358Notes

Reaction equation

[CH:1]1([SH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:8]1[N:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:9]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Cl:23][C:21]1[CH:20]=[CH:19][C:9]([C:10]([NH:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:11])=[C:8]([S:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Cyclopentanethiol (7.84 mL, 73.22 mmol) was added in one portion to 2,6-dichloro-N-cyclohexylnicotinamide (20 g, 73.22 mmol) and sodium carbonate (23.28 g, 219.65 mmol) in DMF (150 mL). The resulting suspension was stirred at 60° C. for 3 hours. The mixture was cooled, evaporated, DCM (250 mL) was added and the mixture was washed with water (3×100 mL) and brine (50 mL), dried (MgSO4), filtered and evaporated to a sticky pale yellow solid. This was triturated with 4:1 hexane:ethyl acetate, filtered and dried to give 6-chloro-N-cyclohexyl-2-(cyclopentylthio)nicotinamide (13.8 g, 55.6%) as a white solid.

Workup

temperatureThe mixture was cooled
customevaporated
additionDCM (250 mL) was added
washthe mixture was washed with water (3×100 mL) and brine (50 mL)
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated to a sticky pale yellow solid
customThis was triturated with 4:1 hexane
filtrationethyl acetate, filtered
customdried

Sources & evidence

ORD record: ord-251e941e15f049deaffcdcb52447824d
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673938B2

Reaction notes

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