4-(1-Pyrrolidinyl)piperidine → [4-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517074Notes

Reaction equation

HRID 1517074 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[CH:6][N:5]=[C:4]([C:18](O)=[O:19])[C:3]=1[CH3:21].COC(C1C(C)=C(Cl)C(C2C=CC=C(C(F)(F)F)C=2)=CN=1)=O.CC1C(C(O)=O)=NC=C(C2C=CC=C(C(F)(F)F)C=2)C=1.[N:64]1([CH:69]2[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]2)[CH2:68][CH2:67][CH2:66][CH2:65]1>>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)=[CH:6][N:5]=[C:4]([C:18]([N:72]2[CH2:73][CH2:74][CH:69]([N:64]3[CH2:68][CH2:67][CH2:66][CH2:65]3)[CH2:70][CH2:71]2)=[O:19])[C:3]=1[CH3:21]

Participants

5

Reactant 4

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 574411243-Methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acidHCID 670253894-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester2×HCID 866374214-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid

Product 1

HCID 57441144[4-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Procedure

In analogy to the procedure described for example 1, 4-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid [prepared from 4-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester (intermediate 3) by saponification in analogy to the procedure described for intermediate 1B] was reacted with 4-pyrrolidin-1-yl-piperidine to give the title compound as colorless solid. MS: 452.1 (MH+, 1Cl).

Sources & evidence

ORD record
ord-81be8d1fbdd3415c80457870a20c52a3
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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