Acetic Anhydride → HCID 10004528, compound

HRID 1791340Notes

Reaction equation

HRID 1791340 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]([CH3:28])([CH3:27])[CH2:9][C:10]([NH2:26])([CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[C:11]([F:14])([F:13])[F:12])[CH:7]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>ClC(Cl)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]([CH3:27])([CH3:28])[CH2:9][C:10]([NH:26][C:31](=[O:33])[CH3:32])([CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[C:11]([F:12])([F:14])[F:13])[CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10319953HCID 10319953, compound

Product 1

HCID 10004528HCID 10004528, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 3-(5-fluoro-2-methoxy-phenyl)-3-methyl-1-quinolin-4-ylmethyl-1-trifluoromethyl-butylamine (42.0 mg, 0.1 mmol) in dichloroethane (4 mL) was treated with acetic anhydride (71 μL, 1.0 mmol). The mixture was stirred for 16 h at 85° C. and quenched with NaHCO3 (sat, 4 mL). Phases were separated and the aqueous layer was extracted with CHCl3 (3×2 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified on SiO2 (50%–70%, EtOAc:hexanes) to give 34.0 mg (74%) of the title product.

Workup

  1. customquenched with NaHCO3 (sat, 4 mL)
  2. customPhases were separated
  3. extractionthe aqueous layer was extracted with CHCl3 (3×2 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on SiO2 (50%–70%, EtOAc:hexanes)

Sources & evidence

ORD record
ord-06a1b845d841460fa85679daee335f1f
Source dataset
uspto-grants-2006_07
Patent number
US07074806B2

Reaction notes

Loading…