Acetic Anhydride → HCID 68153023, compound

HRID 2047253Notes

Reaction equation

HRID 2047253 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[C:9]([C:32]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=2[Cl:39])=[N:10][O:11][C:12]=1[C:13]1[CH:14]=[N:15][N:16]([C:22]2[CH:23]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:25]=[CH:26][CH:27]=2)[C:17]=1[C:18]([F:21])([F:20])[F:19])=[O:7])(=O)[CH3:2].C(OC(=O)C)(=O)C>C(O)(=O)C.O>[Cl:39][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]([F:38])[C:32]=1[C:9]1[C:8]([C:6]2[O:7][C:1]([CH3:2])=[N:4][N:5]=2)=[C:12]([C:13]2[CH:14]=[N:15][N:16]([C:22]3[CH:23]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:25]=[CH:26][CH:27]=3)[C:17]=2[C:18]([F:20])([F:19])[F:21])[O:11][N:10]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 68153068HCID 68153068, compound

Product 1

HCID 68153023HCID 68153023, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

The intermediate N-(3-(4-(4-(2-acetylhydrazinecarbonyl)-3-(2-chloro-6-fluorophenyl) isoxazol-5-yl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)acetamide (25.0 mg, 0.044 mmol) was dissolved in acetic acid (1.50 mL). Acetic anhydride (104 μL, 1.1 mmol) was added and the reaction mixture was heated in the microwave to 140° C. for 8 h. The reaction mixture was diluted with water (40 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with water (10 mL), dried over Na2SO4 and concentrated in vacuo.

Workup

  1. extractionextracted with CH2Cl2 (3×20 mL)
  2. washThe combined organic layers were washed with water (10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33e8c3792396427ca39c681117388c28
Source dataset
uspto-grants-2013_11
Patent number
US08592456B2

Reaction notes

Loading…