[Cyclopropyl-(3-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester → [3-Cyclopropyl-5-(1H-pyrazol-4-yl)-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 545437Notes

Reaction equation

HRID 545437 reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21](OC(F)(F)F)=[CH:20][CH:19]=3)[N:15]([CH:29]3[CH2:31][CH2:30]3)[C:14]=2[C:32]([N:34]2[CH2:39][CH2:38][CH:37]([N:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)[CH2:36][CH2:35]2)=[O:33])[CH:10]=[N:9]1)C1C=CC=CC=1.C(OC(=O)CN(C1CC1)C(=O)C1C=CC=C([O:58][C:59]([F:62])([F:61])[F:60])C=1)C>[Pd]>[CH:29]1([N:15]2[C:14]([C:32]([N:34]3[CH2:35][CH2:36][CH:37]([N:40]4[CH2:41][CH2:42][CH2:43][CH2:44]4)[CH2:38][CH2:39]3)=[O:33])=[C:13]([C:11]3[CH:10]=[N:9][NH:8][CH:12]=3)[N:17]=[C:16]2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:58][C:59]([F:62])([F:61])[F:60])[CH:19]=2)[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 67132963[Cyclopropyl-(3-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl esterHCID 67133194[5-(1-benzyl-1H-pyrazol-4-yl)-3-cyclopropyl-2-(4-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Product 1

HCID 57541144[3-Cyclopropyl-5-(1H-pyrazol-4-yl)-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In analogy to the procedure described in example 95, the title compound has been obtained from [5-(1-benzyl-1H-pyrazol-4-yl)-3-cyclopropyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (prepared in analogy to the sequence described for the preparation of intermediate 13, but using [cyclopropyl-(3-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester instead of [cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester in step 13A) by hydrogenation with 10% palladium on charcoal to give the title compound as colorless amorphous solid. MS: 515.2 (MH+).

Workup

  1. customprepared in analogy to the sequence

Sources & evidence

ORD record
ord-30625168ea884b52b44d63a4990f06be
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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