Ethyl Acetate → HCID 90409251, compound

HRID 589019Notes

Reaction equation

HRID 589019 reaction equation
[C:1]1([CH:7]2[NH:12][C:11]3=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=[C:10]3[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1N=CN([C:32](N2C=NC=C2)=[O:33])C=1.CCOC(C)=O>C1COCC1>[C:1]1([CH:7]2[N:12]3[C:32](=[O:33])[NH:17][C:13]4=[CH:14][CH:15]=[CH:16][C:10](=[C:11]34)[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 904094562H-1,4-Benzoxazin-5-amine, 3,4-dihydro-3-phenyl-

Product 1

HCID 90409251HCID 90409251, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

The 3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-5-amine (0.95 g, 4.2 mmol) was dissolved in THF (30 mL) and DIPEA (1.5 mL, 8.4 mmol) at room temperature (room temperature). The N,N-carbonyldiimidazole (0.82 g, 5.0 mmol) was added portion wise over 10 min. The reaction was heated to 70° C. for 1 h and allowed to cool to room temperature and stirred overnight. To the reaction mixture was added EtOAc, and then the mixture was washed with water, sodium bicarbonate water and brine, then dried over magnesium sulfate and concentrated to give crude product as a dark oil. The oil was triturated with ethyl ether to give a precipitate. The solids were triturated twice with ethyl ether and then the solids were collected and air dried to give 4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one as a brown solid (0.51 g, 48%). LCMS calc. for C15H13N2O2 (M+H)+: m/z=253.1. found: 253.1. 1H NMR (300 MHz, DMSO-d6) δ 10.88 (s, 1H), 7.39-7.22 (m, 3H), 7.15-7.04 (m, 2H), 6.88 (t, J=8.0 Hz, 1H), 6.67 (d, J=7.8 Hz, 1H), 6.57 (d, J=8.2 Hz, 1H), 5.45 (s, 1H), 4.54 (dd, J=11.6, 2.2 Hz, 1H), 4.37 (dd, J=11.6, 3.0 Hz, 1H).

Workup

  1. customat room temperature
  2. custom(room temperature)
  3. temperatureto cool to room temperature
  4. washthe mixture was washed with water, sodium bicarbonate water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give crude product as a dark oil
  8. customThe oil was triturated with ethyl ether
  9. customto give a precipitate
  10. customThe solids were triturated twice with ethyl ether
  11. customthe solids were collected
  12. customair dried

Sources & evidence

ORD record
ord-a511034b3d4842cfae11497429275087
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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