Ethyl Acetate → HCID 90410171, compound

HRID 589021Notes

Reaction equation

HRID 589021 reaction equation
[Br:1][C:2]1[C:11]2[O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:7]3[C:18](=[O:20])[NH:19][C:5]([C:6]=23)=[CH:4][CH:3]=1.Cl.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[H-].[Na+].CCOC(C)=O>CN(C=O)C.O>[Br:1][C:2]1[C:11]2[O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:7]3[C:18](=[O:20])[N:19]([CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[C:5]([C:6]=23)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 90409014HCID 90409014, compound

Product 1

HCID 90410171HCID 90410171, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a 0° C. mixture of 7-bromo-4-phenyl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (0.065 g, 0.20 mmol) from Example 1, step 4 and 4-(2-chloroethyl)morpholine hydrochloride (0.12 g, 0.63 mmol) in DMF (1 mL) was added NaH in mineral oil (0.048 g, 1.2 mmol). The reaction mixture was stirred over a weekend. EtOAc and water were added. The organic layer was washed with water and brine, dried over Na2SO4 and evaporated to dryness to give an orange oil. The crude was purified by LCMS (C18 column eluting with a gradient MeCN/H2O containing 0.15% NH4OH at 5 mL/min.) and gave a white solid (7.7 mg, 9% yield). 1H NMR (400 MHz, CD3OD/CDCl3): d 7.31 (3H, m); 7.18 (3H, m); 6.65 (1H, d); 5.19 (1H, m); 4.61 (1H, m); 4.43 (1H, m); 3.99 (2H, m); 3.6 (4H, m); 2.65 (2H, m); 2.51 (4H, m). LCMS calc. for C26H29N4O4 (M+H)+: m/z=. found: 444.1, 446.1.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customto give an orange oil
  5. customThe crude was purified by LCMS (C18 column
  6. washeluting with a gradient MeCN/H2O containing 0.15% NH4OH at 5 mL/min.) and

Sources & evidence

ORD record
ord-df27fa9b4a7a4826b01955676d9c2135
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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