Acetic Anhydride → HCID 59644537, compound

HRID 2251998Notes

Reaction equation

HRID 2251998 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:9]=[N:10][N:11]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=3)[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1[C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[Cl:42])=[O:35].[C:43](OC(=O)C)(=[O:45])[CH3:44].C([O-])(=O)C.[Na+]>>[F:32][C:30]([F:31])([F:33])[C:22]1[CH:21]=[C:20]([CH:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=1)[CH2:19][N:11]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:8]([C:4]2[C:3]([C:34](=[O:35])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:42])=[C:2]([NH:1][C:43](=[O:45])[CH3:44])[CH:7]=[CH:6][N:5]=2)[N:9]=[N:10]1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 10175375HCID 10175375, compound

Product 1

HCID 59644537HCID 59644537, compound

Conditions

Temperature
80 °C

Procedure

Combine {4-amino-2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chloro-phenyl)-methanone (840 mg, 0.067 mmol) and 2.0 ml of acetic anhydride and sodium acetate (18.2 mg, 0.134 mmol). Seal the reaction mixture in a pyrex tube and heat to 80° C. After 13 hours, cool to RT. Pour the mixture through a plug of Celite® (1 cm) and silica gel (2 cm). Concentrate the clear liquid to 1.0 mL and apply to a 2 mm chromatotron plate and elute with a EtOAc/hexane gradient to provide 26 mg of the title compound: Exact Mass 643.1; mass spectrum (IS): m/z=643.9 (M+1), m/z=641.8 (M−1); 1H NMR (250 MHz, CDCl3) 9.69 (s, 0.6H), 8.39 (s, 1H), 7.74 (s, 1H), 7.15-7.49 (m, 5H), 7.27 (s, 2H), 6.80-7.05 (m, 5H), 5.26 (s, 2H), 2.16 (s, 3H).

Workup

  1. customSeal the reaction mixture in a pyrex tube
  2. temperaturecool to RT
  3. additionPour the mixture through a plug of Celite® (1 cm) and silica gel (2 cm)
  4. concentrationConcentrate the clear liquid to 1.0 mL
  5. washapply to a 2 mm chromatotron plate and elute with a EtOAc/hexane gradient

Sources & evidence

ORD record
ord-757bf4ceb1534aba8cc684f6c3b76b5e
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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