Propyl mercaptan → N-adamantan-1-yl-6-chloro-2-(propylthio)nicotinamide

HRID 1187376Notes

Reaction equation

[CH2:1]([SH:4])[CH2:2][CH3:3].[C:5]12([NH:15][C:16](=[O:25])[C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[N:19][C:18]=3Cl)[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2.C(=O)([O-])[O-].[K+].[K+]>C(#N)CCC.CCOC(C)=O>[C:5]12([NH:15][C:16](=[O:25])[C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[N:19][C:18]=3[S:4][CH2:1][CH2:2][CH3:3])[CH2:6][CH:7]3[CH2:8][CH:9]([CH2:10][CH:11]([CH2:13]3)[CH2:12]1)[CH2:14]2

Participants

Conditions

Temperature: 150 °C

Procedure

1-Propanethiol (0.499 mL, 5.50 mmol) was added dropwise to N-adamantan-1-yl-2,6-dichloronicotinamide (1.63 g, 5 mmol) and potassium carbonate (2.07 g, 15.00 mmol) in butyronitrile (15 mL) at 20° C. over a period of 2 minutes under nitrogen. The resulting suspension was heated at 150° C. for 2 hours. The reaction mixture was diluted with EtOAc (60 mL), and washed sequentially with water (20 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford N-adamantan-1-yl-6-chloro-2-(propylthio)nicotinamide (2.21 g, 100%) as a white solid.

Workup

washwashed sequentially with water (20 mL) and saturated brine (20 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-e610635a944444e5a3f923bb71b4da43
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673938B2

Reaction notes

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