4-Toluenesulfonyl chloride → 5-Amino-1-(3,5-bis-trifluoromethyl-benzyl)-1H-imidazole-4-carbonitrile

HRID 349267Notes

Reaction equation

HRID 349267 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=2)[CH:5]=[N:4][C:3]=1[C:22]([NH2:24])=O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=2)[CH:5]=[N:4][C:3]=1[C:22]#[N:24]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 866012195-Amino-1-(3,5-bis-trifluoromethyl-benzyl)-1H-imidazole-4-carboxylic acid amide

Product 1

HCID 866012205-Amino-1-(3,5-bis-trifluoromethyl-benzyl)-1H-imidazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Combine 5-Amino-1-(3,5-bis-trifluoromethyl-benzyl)-1H-imidazole-4-carboxylic acid amide (0.106 g, 0.30 mmol) and p-toluenesulfonyl chloride (0.069 g, 0.36 mmol) in pyridine (0.1 M), and stir at RT. After 2 h, quench the reaction with MeOH and concentrate. Redissolve in EtOAc, wash with H2O and brine, then dry (MgSO4), filter, and concentrate. Purify by radial chromatography on silica gel to give the title compound. MS (ES) 335.1 (M+1); 1H NMR (300 MHz, CD3OD): δ 7.96 (s, 1H), 7.77 (s, 2H), 7.37 (s, 1H), 5.31 (s, 2H).

Workup

  1. customquench
  2. customthe reaction with MeOH
  3. concentrationconcentrate
  4. dissolutionRedissolve in EtOAc
  5. washwash with H2O and brine
  6. dry with materialdry (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify by radial chromatography on silica gel

Sources & evidence

ORD record
ord-bcae62e3d2374c15881c6a100674aab6
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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