4-(1-Pyrrolidinyl)piperidine → [2,4-Dimethyl-6-(3-trifluoromethoxy-phenyl)-pyridin-3-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1692420Notes

Reaction equation

HRID 1692420 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)[CH:8]=[C:7]([CH3:22])[C:3]=1[C:4]([OH:6])=O.[N:23]1([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH2:27][CH2:26][CH2:25][CH2:24]1>>[CH3:1][C:2]1[C:3]([C:4]([N:31]2[CH2:32][CH2:33][CH:28]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:29][CH2:30]2)=[O:6])=[C:7]([CH3:22])[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:19])([F:20])[F:21])[CH:12]=2)[N:10]=1

Participants

3

Reactant 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 669015362,4-Dimethyl-6-(3-trifluoromethoxy-phenyl)-nicotinic acid

Product 1

HCID 57580524[2,4-Dimethyl-6-(3-trifluoromethoxy-phenyl)-pyridin-3-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Procedure

In analogy to the procedures described for example 1, for intermediate 5B and for intermediate 1, the title compound has been prepared by the following reaction sequence: i) 6-chloro-2,4-dimethyl-nicotinic acid ethyl ester [Zhou, Y.; Bridger, G. J.; Skerlj, R. T.; Bogucki, D.; Yang, W.; Bourque, E.; Langille, J.; Li, T.-S.; Metz, M. U.S. Pat. Appl. Publ. (2005), US 2005277668 A1] was reacted with 3-trifluoromethoxy-phenyl boronic to give 2,4-dimethyl-6-(3-trifluoromethoxy-phenyl)-nicotinic acid ethyl ester; ii) 2,4-dimethyl-6-(3-trifluoromethoxy-phenyl)-nicotinic acid ethyl ester has been saponified to give 2,4-dimethyl-6-(3-trifluoromethoxy-phenyl)-nicotinic acid; iii) 2,4-dimethyl-6-(3-trifluoromethoxy-phenyl)-nicotinic acid was converted into its acid chloride and reacted with 4-pyrrolidin-1-yl-piperidine to give the title compound as light yellow oil. MS: 448.2 (MH+).

Sources & evidence

ORD record
ord-7d38f2f4bbcc4c7bb52acd495769275e
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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