(4,6-Dimethyl-5'-trifluoromethyl-[2,3']bipyridinyl-5-yl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone → benzoic acid (S)-1-[1-(4,6-dimethyl-5'-trifluoromethyl-[2,3']bipyridinyl-5-carbonyl)-piperidin-4-yl]-pyrrolidin-2-ylmethyl ester

HRID 1692430Notes

Reaction equation

HRID 1692430 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])[N:27]=[C:26]([C:44]2[CH:45]=[N:46][CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=2)[CH:25]=1.N1CCC(N2CCC[C@H]2[CH2:65][O:66][C:67](=[O:74])[C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=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[CH2:65][O:66][C:67](=[O:74])[C:68]3[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=3)[CH2:34][CH2:33]2)=[O:31])=[C:28]([CH3:43])[N:27]=[C:26]([C:44]2[CH:45]=[N:46][CH:47]=[C:48]([C:50]([F:52])([F:53])[F:51])[CH:49]=2)[CH:25]=1

Participants

4

Reactant 3

HCID 57580540(4,6-Dimethyl-5'-trifluoromethyl-[2,3']bipyridinyl-5-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 66901608benzoic acid (S)-1-[1-(4,6-dimethyl-5'-trifluoromethyl-[2,3']bipyridinyl-5-carbonyl)-piperidin-4-yl]-pyrrolidin-2-ylmethyl ester

Procedure

In analogy to the procedures described for intermediate 1 and for intermediate 4B,4,6-dimethyl-5′-trifluoromethyl-[2,3′]bipyridinyl-5-carboxylic acid (example 42) 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-(4,6-dimethyl-5′-trifluoromethyl-[2,3′]bipyridinyl-5-carbonyl)-piperidin-4-yl]-pyrrolidin-2-ylmethyl ester, which was subsequently saponified to give the title compound as colorless amorphous solid. MS: 463.2 (MH+).

Sources & evidence

ORD record
ord-92933410d2e84c11881e84f7be144aa9
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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