[2,4-Dimethyl-6-(3-trifluoromethoxy-phenyl)-pyridin-3-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone → benzoic acid (S)-1-{1-[2,4-dimethyl-6-(3-trifluoromethoxy-phenyl)-pyridine-3-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester

HRID 1692421Notes

Reaction equation

HRID 1692421 reaction equation
BrC1C=C(C)C(C(N2CCC(N3CCCC3)CC2)=O)=C(C)C=1.[CH3:23][C:24]1[C:29]([C:30]([N:32]2[CH2:37][CH2:36][CH:35]([N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:34][CH2:33]2)=[O:31])=[C:28]([CH3:43])[CH:27]=[C:26]([C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([O:50][C:51]([F:54])([F:53])[F:52])[CH:45]=2)[N:25]=1.N1CCC(N2CCC[C@H]2[CH2:66][O:67][C:68](=[O:75])[C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)CC1>>[CH3:23][C:24]1[C:29]([C:30]([N:32]2[CH2:37][CH2:36][CH:35]([N:38]3[CH2:39][CH2:40][CH2:41][C@H:42]3[CH2:66][O:67][C:68](=[O:75])[C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)[CH2:34][CH2:33]2)=[O:31])=[C:28]([CH3:43])[CH:27]=[C:26]([C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([O:50][C:51]([F:53])([F:54])[F:52])[CH:45]=2)[N:25]=1

Participants

4

Reactant 3

HCID 57580524[2,4-Dimethyl-6-(3-trifluoromethoxy-phenyl)-pyridin-3-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneHCID 66901590benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester2×HCID 66901599(4-Bromo-2,6-dimethyl-phenyl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Product 1

HCID 66901636benzoic acid (S)-1-{1-[2,4-dimethyl-6-(3-trifluoromethoxy-phenyl)-pyridine-3-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester

Procedure

In analogy to the procedures described for intermediate 1 and for intermediate 4B,2,4-dimethyl-6-(3-trifluoromethoxy-phenyl)-nicotinic acid (example 28) was converted into its acid chloride and reacted with benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester (intermediate 3) to give benzoic acid (S)-1-{1-[2,4-dimethyl-6-(3-trifluoromethoxy-phenyl)-pyridine-3-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester, which was subsequently saponified to give the title compound as colorless amorphous solid. MS: 478.2 (MH+).

Sources & evidence

ORD record
ord-31b2fcefc74f458f8fc1edee0a0a7c3a
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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