Piperidine → 2-(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-1-[4-(4-chloro-phenyl)-4-(piperidine-1-carbonyl)-piperidin-1-yl]-ethanone

HRID 2104239Notes

Reaction equation

HRID 2104239 reaction equation
[Cl:1][C:2]1[C:3]([C:27]([F:30])([F:29])[F:28])=[N:4][N:5]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][C:14]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)([C:17]([OH:19])=O)[CH2:13][CH2:12]2)=[O:10])[C:6]=1[CH3:7].[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN1C(=O)CCC1>[Cl:1][C:2]1[C:3]([C:27]([F:28])([F:29])[F:30])=[N:4][N:5]([CH2:8][C:9]([N:11]2[CH2:12][CH2:13][C:14]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)([C:17]([N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:19])[CH2:15][CH2:16]2)=[O:10])[C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 16128275HCID 16128275, compound

Product 1

HCID 161284342-(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-1-[4-(4-chloro-phenyl)-4-(piperidine-1-carbonyl)-piperidin-1-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 4 mL vial was added 50 mg of 1-[2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carboxylic acid (0.11 mmol, 1.0 equiv), 13 μL of piperidine (0.13 mmol, 1.2 equiv), 60 μL TEA (0.43 mmol, 4.00 equiv), 71 mg BOP (0.16 mmol, 1.5 equiv), and 500 μL NMP. The resultant mixture was stirred overnight at room temperature and the crude product was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent) to yield 2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-1-[4-(4-chloro-phenyl)-4-(piperidine-1-carbonyl)-piperidin-1-yl]-ethanone:MS (ES) M+H expected=531.4, found=531.1.

Workup

  1. customthe crude product was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent)

Sources & evidence

ORD record
ord-2a4a69e9426b497bbd89e2c4cd6c8583
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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