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

HRID 545428Notes

Reaction equation

HRID 545428 reaction equation
[Na+].[CH:2]1([N:5]2[C:9]([C:10]([O-:12])=O)=[C:8]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[N:7]=[C:6]2[C:19]2[CH:24]=[CH:23][C:22](OC(F)(F)F)=[CH:21][CH:20]=2)[CH2:4][CH2:3]1.C(OC(=O)CN(C1CC1)C(=O)C1C=CC=C([O:43][C:44]([F:47])([F:46])[F:45])C=1)C.[N:53]1([CH:58]2[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]2)[CH2:57][CH2:56][CH2:55][CH2:54]1>>[CH:2]1([N:5]2[C:9]([C:10]([N:61]3[CH2:62][CH2:63][CH:58]([N:53]4[CH2:57][CH2:56][CH2:55][CH2:54]4)[CH2:59][CH2:60]3)=[O:12])=[C:8]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[N:7]=[C:6]2[C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([O:43][C:44]([F:47])([F:46])[F:45])[CH:24]=2)[CH2:3][CH2:4]1

Participants

4

Reactant 3

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 67132963[Cyclopropyl-(3-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl esterHCID 67133057HCID 67133057, compound

Product 1

HCID 57541104[3-Cyclopropyl-5-pyridin-3-yl-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-pyridin-3-yl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid sodium salt (prepared in analogy to the sequence described for the preparation of intermediate 8, but using [cyclopropyl-(3-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester instead of [cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester in step 8A) with 4-pyrrolidin-1-yl-piperidine to give the title compound as a colorless amorphous solid. MS: 526.4 (MH+).

Workup

  1. customprepared in analogy to the sequence

Sources & evidence

ORD record
ord-5434f87ef9914ad6bf7125417c833c13
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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