Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 16128357, compound

HRID 2104237Notes

Reaction equation

HRID 2104237 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](O)=[O:18])[CH2:13][CH2:12]2)=[O:10])[C:6]=1[CH3:7].[CH2:31]([NH:33][CH2:34][CH3:35])[CH3:32].C1COCC1.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>[CH2:31]([N:33]([CH2:34][CH3:35])[C:17]([C:14]1([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[CH2:15][CH2:16][N:11]([C:9](=[O:10])[CH2:8][N:5]2[C:6]([CH3:7])=[C:2]([Cl:1])[C:3]([C:27]([F:30])([F:29])[F:28])=[N:4]2)[CH2:12][CH2:13]1)=[O:18])[CH3:32]

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 16128275HCID 16128275, compoundHCID 19023656THF diethylamine

Product 1

HCID 16128357HCID 16128357, compound

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), 65 μL of 2.0 M diethylamine/THF (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 of NMP. The 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 the desired 1-[2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carboxylic acid diethylamide:.MS (ES) M+H expected=477.3, found=477.4.

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-2d609091e2944e6dbf59735d8245741e
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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