benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester → [5-Chloro-3-methyl-2-(3-trifluoromethyl-phenyl)-3H-imidazol-4-yl]-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone

HRID 545426Notes

Reaction equation

HRID 545426 reaction equation
[Cl:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[N:4]([CH3:17])[C:3]=1[C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:30][CH2:29][CH2:28][C@H:27]2[CH2:31][O:32]C(=O)C2C=CC=CC=2)[CH2:22][CH2:21]1)=[O:19].ClC1N=C(C2C=CC=C(C(F)(F)F)C=2)N(C)C=1C(O)=O.N1CCC(N2CCC[C@H]2COC(=O)C2C=CC=CC=2)CC1>>[Cl:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[N:4]([CH3:17])[C:3]=1[C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:30][CH2:29][CH2:28][C@H:27]2[CH2:31][OH:32])[CH2:22][CH2:21]1)=[O:19]

Participants

4

Reactant 3

HCID 66901590benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester2×HCID 671330255-chloro-3-methyl-2-(3-trifluoromethyl-phenyl)-3H-imidazole-4-carboxylic acidHCID 67133115benzoic acid (S)-1-{1-[5-chloro-3-methyl-2-(3-trifluoromethyl-phenyl)-3H-imidazole-4-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester

Product 1

HCID 57541137[5-Chloro-3-methyl-2-(3-trifluoromethyl-phenyl)-3H-imidazol-4-yl]-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone

Procedure

In analogy to the procedure described for example 73, benzoic acid (S)-1-{1-[5-chloro-3-methyl-2-(3-trifluoromethyl-phenyl)-3H-imidazole-4-carbonyl]-piperidin-4-yl}-pyrrolidin-2-ylmethyl ester [prepared in analogy to the procedure described for example 2 from 5-chloro-3-methyl-2-(3-trifluoromethyl-phenyl)-3H-imidazole-4-carboxylic acid (example 74) and benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester (intermediate 6C)] has been saponified to give the title compound as colorless amorphous solid. MS: 471.2 (MH+, 1Cl).

Workup

  1. customprepared in analogy to the procedure

Sources & evidence

ORD record
ord-c16ace0d0e004daca6887c00c468af95
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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