Acetic Anhydride → HCID 86715643, compound

HRID 928812Notes

Reaction equation

HRID 928812 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:20]3[C:21]([CH3:27])=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=3)([C:14]3[N:18]([CH3:19])[N:17]=[N:16][CH:15]=3)[OH:13])[CH:10]=2)[N:5]=[C:4]([O:28][CH3:29])[C:3]=1[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=1.[H-].[Na+].[C:43](OC(=O)C)(=[O:45])[CH3:44]>CN(C=O)C>[C:43]([O:13][C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([O:28][CH3:29])[C:3]([CH2:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([F:40])([F:38])[F:39])=[CH:35][CH:36]=1)=[C:2]2[Cl:1])([C:20]1[C:21]([CH3:27])=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=1)[C:14]1[N:18]([CH3:19])[N:17]=[N:16][CH:15]=1)(=[O:45])[CH3:44]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 74221202HCID 74221202, compound

Product 1

HCID 86715643HCID 86715643, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol (544 mg, 0.960 mmol, Example 77B) in 20 mL of dry DMF at room temperature was added NaH (75 mg, 1.9 mmol, 60% in mineral oil). After stirring for 20 min, acetic anhydride (0.18 mL, 1.9 mmol) was added. The mixture was stirred for one hour and some suspension formed. After the mixture was quenched with a few drops of water, the suspension was filtered off and the filtrate was concentrated in vacuo. The residue was partitioned between dichloromethane and saturated NaHCO3 (aq). The extracts were dried (Na2SO4), filtered, and concentrated to give the title compound as a semi-solid.

Workup

  1. stirringThe mixture was stirred for one hour
  2. customsome suspension formed
  3. customAfter the mixture was quenched with a few drops of water
  4. filtrationthe suspension was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was partitioned between dichloromethane and saturated NaHCO3 (aq)
  7. dry with materialThe extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-eff7321cb98246609d9c730232d30892
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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