3-Methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid → benzoic acid (S)-1-{1-[3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester

HRID 1517075Notes

Reaction equation

HRID 1517075 reaction equation
[CH3:1][C:2]1[C:3]([C:18]([OH:20])=O)=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH:7]=1.[NH:21]1[CH2:26][CH2:25][CH:24]([N:27]2[CH2:31][CH2:30][CH2:29][C@H:28]2[CH2:32][O:33][C:34](=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:23][CH2:22]1>>[CH3:1][C:2]1[C:3]([C:18]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]3[CH2:31][CH2:30][CH2:29][C@H:28]3[CH2:32][O:33][C:34](=[O:41])[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:23][CH2:22]2)=[O:20])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 574411243-Methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid3×HCID 66901590benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester2×

Product 1

HCID 67025992benzoic acid (S)-1-{1-[3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester

Procedure

In analogy to the procedures described for example 1 and for intermediate 1B, 3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid (intermediate 1B) was reacted with benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester (intermediate 6) to give benzoic acid (S)-1-{1-[3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester, which was subsequently saponified to give the title compound as light brown solid. MS: 448.1 (MH+).

Sources & evidence

ORD record
ord-3302e077f8794aa6b6085665462df6cd
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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