Diisopropylethylamine → 2-(3-Chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-ol

HRID 2277159Notes

Reaction equation

HRID 2277159 reaction equation
Cl.[NH2:2][C:3]1[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][C:4]=1[OH:10].[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH:23]1[CH2:25][CH2:24]1)[C:15](O)=O.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([C:15]2[O:10][C:4]3[CH:5]=[C:6]([OH:7])[CH:8]=[CH:9][C:3]=3[N:2]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH:23]1[CH2:24][CH2:25]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 134088224-Aminobenzene-1,3-diol hydrochlorideHCID 613797813-chloro-4-(cyclopropylmethoxy)Benzoic acid

Product 1

HCID 867312122-(3-Chloro-4-(cyclopropylmethoxy)phenyl)-1,3-benzoxazol-6-olYield 11.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-aminoresorcinol hydrochloride (5.00 g), 3-chloro-4-(cyclopropylmethoxy)benzoic acid (6.38 g) and diisopropylethylamine (7.37 mL) in DMF (50 mL) was added HATU (11.8 g), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To a suspension of the obtained residue, hexachloroethane (16.7 g) and triphenylphosphine (18.5 g) in acetonitrile (50 mL) was added triethylamine (11.8 mL), and the mixture was stirred at room temperature for 15 min, and then with heating at 80° C. for 2 hr. The reaction mixture was filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.00 g).

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. additionTo a suspension of the obtained residue, hexachloroethane (16.7 g) and triphenylphosphine (18.5 g) in acetonitrile (50 mL)
  5. additionwas added triethylamine (11.8 mL)
  6. stirringthe mixture was stirred at room temperature for 15 min
  7. temperaturewith heating at 80° C. for 2 hr
  8. filtrationThe reaction mixture was filtered
  9. customthe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7b380b5e68fc4e23ab1ea8545b958b58
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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