Water → HCID 44602986, compound

HRID 453941Notes

Reaction equation

HRID 453941 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:14]=[C:13]([CH3:15])[C:11]([NH2:12])=[C:10]([CH3:16])[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26]([CH2:30][C:31](Cl)=[O:32])([CH3:29])([CH3:28])[CH3:27].O>C(Cl)Cl>[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:14]=[C:13]([CH3:15])[C:11]([NH:12][C:31](=[O:32])[CH2:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:10]([CH3:16])[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 67083542HCID 67083542, compound

Product 1

HCID 44602986HCID 44602986, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-fluoro-benzyloxy)-2,6-dimethylaniline (0.20 g, 0.82 mmol) from above and triethylamine (125 mg, 1.24 mmol) in anhydrous methylene chloride (20 ml) was added dropwise tert-butylacetyl chloride (135 mg, 1 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture, and the mixture was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ISCO, hexane/EtOAc, 0-40%, 40 min) and recrystallized from hexane/EtOAc (5:1) to give 230 mg (82%) of the white solids. 1H NMR (DMSO-d6, 400 MHz): δ 8.92 (brs, 1H, exchangeable with D20, NH), 7.46 (dd, J=4.7 and 6.4 Hz, 2H), 7.19 (t, J=7.0 Hz, 2H), 6.70 (s, 2H), 5.02 (s, 2H), 2.16 (s, 2H), 2.08 (s, 6H), 1.03 (s, 9H). MS: 344 (M+1).

Workup

  1. washthe mixture was washed with saturated brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ISCO, hexane/EtOAc, 0-40%, 40 min)
  5. customrecrystallized from hexane/EtOAc (5:1)

Sources & evidence

ORD record
ord-dcf2e3bb425b4319b8d800ae1288c460
Source dataset
uspto-grants-2013_07
Patent number
US08492588B2

Reaction notes

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