Ammonium Chloride → HCID 86731283, compound

HRID 2277217Notes

Reaction equation

HRID 2277217 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[CH2:20][CH:19]([O:21][CH2:22][C:23](N5CCOCC5)=[O:24])[CH2:18][CH2:17][C:15]=4[N:16]=3)=[CH:8][C:7]=2[F:31])[CH2:3][CH2:2]1.[CH3:32][Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[CH2:20][CH:19]([O:21][CH2:22][CH:23]([OH:24])[CH3:32])[CH2:18][CH2:17][C:15]=4[N:16]=3)=[CH:8][C:7]=2[F:31])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86731282HCID 86731282, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 86731283HCID 86731283, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-((2-(4-(cyclopropylmethoxy)-3-fluorophenyl)-4,5,6,7-tetrahydro-1,3-benzoxazol-6-yl)oxy)-1-(morpholin-4-yl)ethanone (1.68 g) in THF (25 mL) was added methylmagnesium bromide (1 M THF solution, 5.85 mL). To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the obtained residue in a mixed solvent of THF (10 mL)-methanol (10 mL) was added sodium tetrahydroborate (148 mg), and the mixture was stirred at room temperature for 10 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (920 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. additionTo the obtained residue in a mixed solvent of THF (10 mL)-methanol (10 mL) was added sodium tetrahydroborate (148 mg)
  5. additionTo the reaction mixture was added saturated aqueous ammonium chloride solution
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3ff8e9ac43fb42db9ec02e49c932ca97
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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