Acetic Acid → HCID 90409628, compound

HRID 589058Notes

Reaction equation

HRID 589058 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[N:15]2[C:16](=[O:22])[NH:17][C:18]3=[CH:19][CH:20]=[CH:21][C:13](=[C:14]23)[O:12][CH2:11]1.C(O)(=O)C.C(#N)C>C(OCC)(=O)C>[Br:1][C:21]1[C:13]2[O:12][CH2:11][C:10]([CH3:9])([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:15]3[C:16](=[O:22])[NH:17][C:18]([C:14]=23)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 90408783HCID 90408783, compound

Product 1

HCID 90409628HCID 90409628, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (60 mg, 0.3 mmol) was added to a solution of 4-methyl-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (90 mg, 0.3 mmol), acetic acid (6 mL) and acetonitrile (6 mL) at 0° C. The reaction mixture was stirred for 1 h at 0° C., quenched with water, and was concentrated to give the crude product. The crude product was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate. The combined organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give a dark oil. The product was purified by FCC on silica gel eluting a hexane:ethyl acetate gradient containing 20% ethanol to give 7-bromo-4-methyl-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one as an off white solid (0.090 g. 80%). LCMS calculated for C15H13BrN3O2 (M+H)+: m/z=346.1, 348.1. found: 345.9, 347.9.

Workup

  1. customquenched with water
  2. concentrationwas concentrated
  3. customto give the crude product
  4. washwashed with saturated aqueous sodium bicarbonate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a dark oil
  10. customThe product was purified by FCC on silica gel eluting a hexane
  11. additionethyl acetate gradient containing 20% ethanol

Sources & evidence

ORD record
ord-46d112238dcd418788bfefe22f9db6ee
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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