4-Methylnicotinic acid Hydrochloride → N-[1-((R)-2-cyano-1-methyl-ethyl)-piperidin-4-yl]-4-methyl-N-(4-methylsulfanyl-phenyl)-nicotinamide

HRID 1726308Notes

Reaction equation

HRID 1726308 reaction equation
Cl.[CH3:2][C:3]1[C:8]([C:9]([OH:11])=O)=[CH:7][N:6]=[CH:5][CH:4]=1.[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([C@H:27]([CH3:31])[CH2:28][C:29]#[N:30])[CH2:23][CH2:22]2)=[CH:16][CH:15]=1>>[C:29]([CH2:28][C@H:27]([N:24]1[CH2:23][CH2:22][CH:21]([N:20]([C:17]2[CH:18]=[CH:19][C:14]([S:13][CH3:12])=[CH:15][CH:16]=2)[C:9](=[O:11])[C:8]2[C:3]([CH3:2])=[CH:4][CH:5]=[N:6][CH:7]=2)[CH2:26][CH2:25]1)[CH3:31])#[N:30]

Participants

3

Reactant 2

HCID 27965064-Methylnicotinic acid HydrochlorideHCID 68971966(R)-3-[4-(4-methylsulfanyl-phenylamino)-piperidin-1-yl]-butyronitrile

Product 1

HCID 68973020N-[1-((R)-2-cyano-1-methyl-ethyl)-piperidin-4-yl]-4-methyl-N-(4-methylsulfanyl-phenyl)-nicotinamideYield 70%

Procedure

Using general procedure F, 4-methylnicotinic acid hydrochloride (363 mg, 2.09 mmol) and (R)-3-[4-(4-methylsulfanyl-phenylamino)-piperidin-1-yl]-butyronitrile (see EXAMPLE 307) (304 mg, 0.93 mmol) afforded N-[1-((R)-2-cyano-1-methyl-ethyl)-piperidin-4-yl]-4-methyl-N-(4-methylsulfanyl-phenyl)-nicotinamide as a brown oil (256 mg, 70%).

Sources & evidence

ORD record
ord-54057cc8895b4ac7b659ce845e587c2f
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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