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Phenyl chloroformate → (2R,5S)-N-(2-Bromo-4-pyridyl)-4-(4-cyano-3-trifluoromethylphenyl)-2,5-dimethylpiperazine-1-carboxamide

HRID 1838256
Notes
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Reaction equation

HRID 1838256 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Br:8])[CH:3]=1.Cl[C:10](OC1C=CC=CC=1)=[O:11].[CH3:19][C@H:20]1[CH2:25][NH:24][C@H:23]([CH3:26])[CH2:22][N:21]1[C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29]([C:35]([F:38])([F:37])[F:36])[CH:28]=1>N1C=CC=CC=1>[Br:8][C:4]1[CH:3]=[C:2]([NH:1][C:10]([N:24]2[CH2:25][C@H:20]([CH3:19])[N:21]([C:27]3[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29]([C:35]([F:38])([F:37])[F:36])[CH:28]=3)[CH2:22][C@H:23]2[CH3:26])=[O:11])[CH:7]=[CH:6][N:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 3464554-Amino-2-bromopyridineHCID 11391932trans-4-(2,5-Dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile

Product 1

HCID 86590778(2R,5S)-N-(2-Bromo-4-pyridyl)-4-(4-cyano-3-trifluoromethylphenyl)-2,5-dimethylpiperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Procedure

A 1.66 g portion of 4-amino-2-bromopyridine was dissolved in 1.4 ml of pyridine, mixed with 2.0 g of phenyl chloroformate and stirred at room temperature for 4 days. Next, this was mixed with 2 g of (2S,5R)-4-(2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile synthesized in Reference Example 11-1 and heated at 100° C. for 1 hour and 30 minutes. After evaporation of the solvent, the residue was dissolved in ethyl acetate, washed with water and then with saturated brine and dried over magnesium sulfate. After evaporation of the solvent, the residue was subjected to a silica gel column chromatography and eluted with chloroform-methanol (30:1, v/v), and the resulting fraction was subjected to crystallization from ethyl acetate-hexane to obtain 2.7 g of the title compound.

Workup

  1. customsynthesized in Reference Example 11-1
  2. temperatureheated at 100° C. for 1 hour and 30 minutes
  3. customAfter evaporation of the solvent
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialwith saturated brine and dried over magnesium sulfate
  7. customAfter evaporation of the solvent
  8. washeluted with chloroform-methanol (30:1
  9. customv/v), and the resulting fraction was subjected to crystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-50d3ac1f869e4934999bd8dfeac51b0f
Source dataset
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06673799B1

Reaction notes

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