((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochloride → [4-((s)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-methyl-3-pyridin-4-yl-1-(3-trifluoromethyl-phenyl)-1h-pyrazol-4-yl]-methanone

HRID 1011978Notes

Reaction equation

HRID 1011978 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[C:3]=1[C:23](O)=[O:24].Cl.Cl.[NH:28]1[CH2:33][CH2:32][CH:31]([N:34]2[CH2:38][CH2:37][CH2:36][C@H:35]2[CH2:39][OH:40])[CH2:30][CH2:29]1>>[OH:40][CH2:39][C@@H:35]1[CH2:36][CH2:37][CH2:38][N:34]1[CH:31]1[CH2:32][CH2:33][N:28]([C:23]([C:3]2[C:4]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)=[N:5][N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:8]=3)[C:2]=2[CH3:1])=[O:24])[CH2:29][CH2:30]1

Participants

3

Reactant 2

HCID 66901571((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochlorideHCID 673152345-methyl-3-pyridin-4-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 57555076[4-((s)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-methyl-3-pyridin-4-yl-1-(3-trifluoromethyl-phenyl)-1h-pyrazol-4-yl]-methanoneYield 14%

Procedure

In analogy to the procedure described in Example 160E], 5-methyl-3-pyridin-4-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acid (Example 160D]) and ((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanoldihydrochloride (Example 161A]) gave the title compound as a light yellow oil (14%). MS: 514.0 (MH+).

Sources & evidence

ORD record
ord-272ec71788404987bac86965c451b07c
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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