Water → HCID 86668196, compound

HRID 243804Notes

Reaction equation

HRID 243804 reaction equation
[NH2:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([CH:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.Cl[C:23]([O:25][CH2:26][C:27]([Cl:30])([Cl:29])[Cl:28])=[O:24].C(N(CC)C(C)C)(C)C.O>C1COCC1>[CH3:21][O:20][C:3]1[C:4]([CH:14]([OH:19])[C:15]([F:18])([F:16])[F:17])=[CH:5][C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:7][C:2]=1[NH:1][C:23](=[O:24])[O:25][CH2:26][C:27]([Cl:30])([Cl:29])[Cl:28]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 68107018HCID 68107018, compound

Product 1

HCID 86668196HCID 86668196, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(3-amino-2-methoxy-5-morpholinophenyl)-2,2,2-trifluoroethanol (2.35 g, 7.67 mmol) in THF (20.4 mL), 2,2,2-trichloroethyl chloroformate (1.14 mL, 8.28 mmol), N,N-diisopropylethylamine (4.02 mL, 23.0 mmol) was added, and the mixture was stirred at 0° C. for 15 minutes. Water was added to the reaction solution and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and filtered, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20-60/40) to obtain 3.45 g (93% yield) of the captioned compound.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20-60/40)

Sources & evidence

ORD record
ord-aa26d8f9a479482b8faee11409ca6e90
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

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