((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochloride → [5-Cyclopropyl-3-pyridin-4-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanone

HRID 1011974Notes

Reaction equation

HRID 1011974 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)[N:7]=[C:6]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:5]=2[C:25](O)=[O:26])[CH2:3][CH2:2]1.Cl.Cl.[NH:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH2:40][CH2:39][CH2:38][C@H:37]2[CH2:41][OH:42])[CH2:32][CH2:31]1>>[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:18])[F:17])[CH:10]=3)[N:7]=[C:6]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:5]=2[C:25]([N:30]2[CH2:31][CH2:32][CH:33]([N:36]3[CH2:40][CH2:39][CH2:38][C@H:37]3[CH2:41][OH:42])[CH2:34][CH2:35]2)=[O:26])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 66901571((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochlorideHCID 673152275-cyclopropyl-3-pyridin-4-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 25206420[5-Cyclopropyl-3-pyridin-4-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-[4-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-methanoneYield 54%

Procedure

In analogy to the procedure described in Example 160E), 5-cyclopropyl-3-pyridin-4-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acid (Example 165B]) and ((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochloride (Example 161A]) gave the title compound as a light yellow solid (54%). MS: 539.8 (MH+).

Sources & evidence

ORD record
ord-1a5fa3900aa04bb4a5be8d54f96c20b2
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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