4-(1-Pyrrolidinyl)piperidine → [5-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1011990Notes

Reaction equation

HRID 1011990 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:18]=[N:19][CH:20]=[N:21][CH:22]=2)[C:3]=1[C:23]([OH:25])=O.[Br:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:37]([CH3:38])=[C:36]([C:39](O)=[O:40])[C:35]([C:42]3[CH:43]=[N:44][CH:45]=[N:46][CH:47]=3)=[N:34]2)=[CH:29][C:28]=1[C:48]([F:51])([F:50])[F:49].[N:52]1([CH:57]2[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]2)[CH2:56][CH2:55][CH2:54][CH2:53]1>>[Br:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:37]([CH3:38])=[C:36]([C:39]([N:60]3[CH2:61][CH2:62][CH:57]([N:52]4[CH2:56][CH2:55][CH2:54][CH2:53]4)[CH2:58][CH2:59]3)=[O:40])[C:35]([C:42]3[CH:43]=[N:44][CH:45]=[N:46][CH:47]=3)=[N:34]2)=[CH:29][C:28]=1[C:48]([F:50])([F:49])[F:51].[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=2)[N:5]=[C:4]([C:17]2[CH:18]=[N:19][CH:20]=[N:21][CH:22]=2)[C:3]=1[C:23]([N:60]1[CH2:61][CH2:62][CH:57]([N:52]2[CH2:56][CH2:55][CH2:54][CH2:53]2)[CH2:58][CH2:59]1)=[O:25]

Participants

5

Reactant 3

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 673152105-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acidHCID 673155081-(4-bromo-3-trifluoromethyl-phenyl)-5-methyl-3-pyrimidin-5-yl-1H-pyrazole-4-carboxylic acid

Product 2

HCID 57555011[5-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneYield 20%HCID 57555036[1-(4-bromo-3-trifluoromethyl-phenyl)-5-methyl-3-pyrimidin-5-yl-1H-pyrazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Procedure

In analogy to the procedure described in Example 160E], a mixture of 5-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazole-4-carboxylic acid and 1-(4-bromo-3-trifluoromethyl-phenyl)-5-methyl-3-pyrimidin-5-yl-1H-pyrazole-4-carboxylic acid and 4-(1-pyrrolidinyl)piperidine gave a mixture of the title compounds. Purification by reversed phase HPLC (MeCN:H2O) afforded [1-(4-bromo-3-trifluoromethyl-phenyl)-5-methyl-3-pyrimidin-5-yl-1H-pyrazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (Example 174) and [5-methyl-3-pyrimidin-5-yl-1-(3-trifluoromethyl-phenyl)-1H-pyrazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone as a white solid (20%). MS: 485.4 (MH+).

Workup

  1. customgave
  2. customPurification by reversed phase HPLC (MeCN:H2O)

Sources & evidence

ORD record
ord-3a6746cb6a0d4f6baaad4ec6e9357fdd
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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