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

HRID 545430Notes

Reaction equation

HRID 545430 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][C:16]([S:19][CH3:20])=[N:17][CH:18]=3)[N:7]=[C:6]2[C:21]2[CH:26]=[CH:25][C:24](OC(F)(F)F)=[CH:23][CH:22]=2)[CH2:4][CH2:3]1.C(OC(=O)CN(C1CC1)C(=O)C1C=CC=C([O:45][C:46]([F:49])([F:48])[F:47])C=1)C.[N:55]1([CH:60]2[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)[CH2:59][CH2:58][CH2:57][CH2:56]1>>[CH:2]1([N:5]2[C:9]([C:10]([N:63]3[CH2:64][CH2:65][CH:60]([N:55]4[CH2:59][CH2:58][CH2:57][CH2:56]4)[CH2:61][CH2:62]3)=[O:12])=[C:8]([C:13]3[CH:14]=[N:15][C:16]([S:19][CH3:20])=[N:17][CH:18]=3)[N:7]=[C:6]2[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([O:45][C:46]([F:49])([F:48])[F:47])[CH:26]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 67132963[Cyclopropyl-(3-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl esterHCID 671332443-Cyclopropyl-5-(2-methylsulfanyl-pyrimidin-5-yl)-2-(4-trifluoromethoxy-phenyl)-3h-imidazole-4-carboxylic acid sodium salt

Product 1

HCID 57541111[3-Cyclopropyl-5-(2-methylsulfanyl-pyrimidin-5-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-(2-methylsulfanyl-pyrimidin-5-yl)-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid sodium salt (prepared in analogy to the sequence described for the preparation of intermediate 10, but using [cyclopropyl-(3-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester instead of [cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester in step 10A) with 4-pyrrolidin-1-yl-piperidine to give the title compound as yellow amorphous solid. MS: 573.2 (MH+).

Workup

  1. customprepared in analogy to the sequence

Sources & evidence

ORD record
ord-40cb9ad0dbbb4119a9828dd21f13a436
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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