((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-trifluoromethoxy-phenyl)-1H-pyrazol-4-yl]-methanone

HRID 1011964Notes

Reaction equation

HRID 1011964 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=2)[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[C:3]=1[C:24]([OH:26])=O.Cl.Cl.[NH:29]1[CH2:34][CH2:33][CH:32]([N:35]2[CH2:39][CH2:38][CH2:37][C@H:36]2[CH2:40][OH:41])[CH2:31][CH2:30]1>>[OH:41][CH2:40][C@@H:36]1[CH2:37][CH2:38][CH2:39][N:35]1[CH:32]1[CH2:33][CH2:34][N:29]([C:24]([C:3]2[C:4]([C:18]3[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=3)=[N:5][N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:17])([F:15])[F:16])[CH:8]=3)[C:2]=2[CH3:1])=[O:26])[CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 66901571((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochlorideHCID 673151905-Methyl-3-pyridin-4-yl-1-(3-trifluoromethoxy-phenyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 57554953[4-((S)-2-Hydroxymethyl-pyrrolidin-1-yl)-piperidin-1-yl]-[5-methyl-3-pyridin-4-yl-1-(3-trifluoromethoxy-phenyl)-1H-pyrazol-4-yl]-methanoneYield 78%

Procedure

In analogy to the procedure described in Example 160E], 5-methyl-3-pyridin-4-yl-1-(3-trifluoromethoxy-phenyl)-1H-pyrazole-4-carboxylic acid (Example 160D]) and ((S)-1-piperidin-4-yl-pyrrolidin-2-yl)-methanol dihydrochloride gave the title compound in 78% yield as a light yellow foam. MS: 530.0 (MH+).

Sources & evidence

ORD record
ord-4b66a905311a485b971abe8bffd7c199
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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