tert-butyl 4-(4-methoxyanilino)tetrahydro-1(2H)-pyridinecarboxylate → N-(4-methoxy-phenyl)-4-methyl-N-piperidin-4-yl-nicotinamide

HRID 1726305Notes

Reaction equation

HRID 1726305 reaction equation
Cl.[CH3:2][C:3]1[C:8]([C:9]([OH:11])=O)=[CH:7][N:6]=[CH:5][CH:4]=1.C(OC([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH2:21][CH2:20]1)=O)(C)(C)C>>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([N:25]([CH:22]2[CH2:23][CH2:24][NH:19][CH2:20][CH2:21]2)[C:9](=[O:11])[C:8]2[C:3]([CH3:2])=[CH:4][CH:5]=[N:6][CH:7]=2)=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 2776119tert-butyl 4-(4-methoxyanilino)tetrahydro-1(2H)-pyridinecarboxylateHCID 27965064-Methylnicotinic acid Hydrochloride

Product 1

HCID 68972690N-(4-methoxy-phenyl)-4-methyl-N-piperidin-4-yl-nicotinamide

Procedure

Using general procedure F with 4-methylnicotinic acid hydrochloride (277 mg, 1.60 mmol) and 4-(4-methoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 119) (350 mg, 1.14 mmol) and then using general procedure C afforded N-(4-methoxy-phenyl)-4-methyl-N-piperidin-4-yl-nicotinamide as a white solid (181 mg, 49% over 2 steps).

Sources & evidence

ORD record
ord-7365f47b0b66494dafa3849ef1daa67b
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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