4-(1-Pyrrolidinyl)piperidine → [3-Cyclopropyl-5-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 545427Notes

Reaction equation

HRID 545427 reaction equation
[CH:1]1([N:4]2[C:8]([C:9](O)=[O:10])=[C:7]([CH3:12])[N:6]=[C:5]2C2C=CC(OC(F)(F)F)=CC=2)[CH2:3][CH2:2]1.[F:24][C:25]([F:37])([F:36])[O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)C(Cl)=O.[N:38]1([CH:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH2:42][CH2:41][CH2:40][CH2:39]1>>[CH:1]1([N:4]2[C:8]([C:9]([N:46]3[CH2:47][CH2:48][CH:43]([N:38]4[CH2:42][CH2:41][CH2:40][CH2:39]4)[CH2:44][CH2:45]3)=[O:10])=[C:7]([CH3:12])[N:6]=[C:5]2[C:29]2[CH:33]=[CH:34][CH:35]=[C:27]([O:26][C:25]([F:24])([F:36])[F:37])[CH:28]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 5228543-(Trifluoromethoxy)benzoyl chlorideHCID 671331923-Cyclopropyl-5-methyl-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid

Product 1

HCID 57541132[3-Cyclopropyl-5-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Procedure

In analogy to the procedure described for example 2, the title compound has been obtained by coupling of 3-cyclopropyl-5-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid (prepared in analogy to the sequence described for the preparation of intermediate 7, but using 3-trifluoromethoxy-benzoyl chloride instead of 4-trifluoromethoxy-benzoyl chloride in step 7B) with 4-pyrrolidin-1-yl-piperidine to give the title compound as colorless amorphous solid. MS: 463.3 (MH+).

Workup

  1. customprepared in analogy to the sequence

Sources & evidence

ORD record
ord-9af53e0a04c445ff98e5ca71c15eccef
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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