Triethylamine → HCID 25254413, compound

HRID 1878009Notes

Reaction equation

HRID 1878009 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:11][C:10](=[O:12])[O:9][C:8]([CH2:17][NH2:18])([C:13]([F:16])([F:15])[F:14])[C:7]=2[CH:19]=1.C(N(CC)CC)C.[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1>C1COCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:11][C:10](=[O:12])[O:9][C:8]([CH2:17][NH:18][C:35]([NH:34][C:31]3[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=3)=[O:36])([C:13]([F:15])([F:16])[F:14])[C:7]=2[CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 68487391HCID 68487391, compound

Product 1

HCID 25254413HCID 25254413, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [6-chloro-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methylamine hydrochloride (60 mg, 0.20 mmol) in THF (1 mL), triethylamine (66 μL, 0.47 mmol) and 4-fluorophenyl isocyanate (32 mg, 0.24 mmol) were sequentially added at room temperature. The reaction solution was stirred overnight at room temperature and then concentrated. The residue was purified by thin-layer silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (24 mg, 28%) was obtained as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by thin-layer silica gel column chromatography (ethyl acetate/hexane=1/1), whereby the objective compound (24 mg, 28%)
  3. customwas obtained as a white solid

Sources & evidence

ORD record
ord-09792e1b76f3402aaeab8ddf022aab9c
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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