Ammonia → HCID 20114810, compound

HRID 1483033Notes

Reaction equation

HRID 1483033 reaction equation
C([O-])(=O)C.[NH4+].[O:6]=[C:7]1[N:12]([CH2:13][CH:14]=O)[C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=2[O:9][CH2:8]1.C([BH3-])#[N:21].[Na+].N>CCO>[NH2:21][CH2:14][CH2:13][N:12]1[C:11]2[CH:16]=[CH:17][CH:18]=[CH:19][C:10]=2[O:9][CH2:8][C:7]1=[O:6]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 509908121000771-62-9

Product 1

HCID 20114810HCID 20114810, compoundYield 113.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve ammonium acetate (1.3 g, 16.19 mmol) in EtOH (15.69 mL); add 2-(3-oxo-1,4-benzoxazin-4-yl)acetaldehyde (150 mg, 0.78 mmol), sodium cyanoborohydride (155.7 mg, 2.35 mmol), and aqueous ammonia (32%; 5.64 g, 105.91 mmol). Charge a sealable tube with the mixture and seal the tube. Heat to 80° C. and stir overnight. Thereafter allow the mixture to cool to ambient temperature and remove the solvent under reduced pressure. Add EtOAc; wash with brine; NaHCO3 (saturated, aqueous); dry; filter; and concentrate the filtrate under reduced pressure. Purify via flash column chromatography eluting with a step gradient of 5%, 10% and 20% MeOH in DCM. Combine the desired fractions and remove the solvent under reduced pressure to provide the title compound (170 mg, 80%). MS (m/z): 193 (M+1).

Workup

  1. additionCharge a sealable tube with the mixture
  2. customseal the tube
  3. temperatureto cool to ambient temperature
  4. customremove the solvent under reduced pressure
  5. washwash with brine
  6. customdry
  7. filtrationfilter
  8. concentrationand concentrate the filtrate under reduced pressure
  9. customPurify via flash column chromatography
  10. washeluting with a step gradient of 5%, 10% and 20% MeOH in DCM
  11. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-8852c78ebd51464abed9e20ce99a5d92
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

Loading…