Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 1-[2-(4-Chloro-5-methyl-3-oxazol-2-yl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carbonitrile

HRID 2104234Notes

Reaction equation

HRID 2104234 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]2[O:28][CH:29]=[CH:30][N:31]=2)=[N:19][N:20]([CH2:23][C:24](O)=[O:25])[C:21]=1[CH3:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1>[Cl:16][C:17]1[C:18]([C:27]2[O:28][CH:29]=[CH:30][N:31]=2)=[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 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 229935654-(4-Chlorophenyl)piperidine-4-carbonitrileHCID 59813981(4-Chloro-5-methyl-3-oxazol-2-yl-pyrazol-1-yl)-acetic acid

Product 1

HCID 161282731-[2-(4-Chloro-5-methyl-3-oxazol-2-yl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 4 mL vial was added 75 mg of 4-(4-chloro-phenyl)-piperidine-4-carbonitrile (0.34 mmol, 1.0 equiv), 90 mg of (4-chloro-5-methyl-3-oxazol-2-yl-pyrazol-1-yl)-acetic acid (0.37 mmol, 1.00 equiv), 194 mg HATU (0.51 mmol, 1.5 equiv), 189 μL TEA (1.36 mmol, 4.00 equiv) and 2 mL NMP. A stir bar was placed in the vial and the reaction mixture stirred overnight at room temperature. The crude reaction mixture was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent) to yield 1-[2- (4-chloro-5-methyl-3-oxazol-2-yl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carbonitrile: MS (ES) M+H expected=444.3, found=444.1.

Workup

  1. customA stir bar was placed
  2. customThe crude reaction mixture
  3. customwas purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent)

Sources & evidence

ORD record
ord-ad007071d1124c61bc8ff2ed5c012c52
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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