Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 16048547, compound

HRID 2104230Notes

Reaction equation

HRID 2104230 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl:16][C:17]1[C:18]([C:27]([F:30])([F:29])[F:28])=[N:19][N:20]([CH2:23][C:24](O)=[O:25])[C:21]=1[CH3:22].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:16][C:17]1[C:18]([C:27]([F:29])([F:28])[F:30])=[N:19][N:20]([CH2:23][C:24]([N:11]2[CH2:12][CH2:13][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([C:14]#[N:15])[CH2:9][CH2:10]2)=[O:25])[C:21]=1[CH3:22]

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1876853(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acidHCID 229935654-(4-Chlorophenyl)piperidine-4-carbonitrile

Product 1

HCID 16048547HCID 16048547, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 25 mL flask was added 455 mg of 4-(4-chloro-phenyl)-piperidine-4-carbonitrile (2.06 mmol, 1.0 equiv), 500 mg of (4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid (2.06 mmol, 1.00 equiv), 1.10 g of BOP (2.47 mmol, 1.2 equiv), 1.15 mL TEA (8.24 mmol, 4.00 equiv) and 6 mL NMP. A stir bar was placed in the flask and the reaction solution was stirred overnight at room temperature under N2 atmosphere. The crude product was purified by normal phase HPLC (EtOAc-hexane as the eluent) to yield 1-[2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carbonitrile: MS (ES) M+H expected=445.3, found=445.1.

Workup

  1. customA stir bar was placed in the flask
  2. customThe crude product was purified by normal phase HPLC (EtOAc-hexane as the eluent)

Sources & evidence

ORD record
ord-962c2f822dba462bb9717f507243b06b
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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