Acetic Anhydride → HCID 9996171, compound

HRID 1378757Notes

Reaction equation

HRID 1378757 reaction equation
[CH:1]1([C:4]2[N:8]=[C:7]([C:9]3[N:10]=[CH:11][N:12]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[NH:15][CH2:14][C:13]=34)[O:6][N:5]=2)[CH2:3][CH2:2]1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>C1COCC1>[C:22]([N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]2[CH:11]=[N:10][C:9]([C:7]3[O:6][N:5]=[C:4]([CH:1]4[CH2:3][CH2:2]4)[N:8]=3)=[C:13]2[CH2:14]1)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10468821HCID 10468821, compound

Product 1

HCID 9996171HCID 9996171, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-4,5-dihydroimidazo[1,5-a]quinoxaline (XXXIII, EXAMPLE 101, 0.201 g) and acetic anhydride (3 ml) in THF (0.7 ml) is heated at 80° for 45 min. The reaction mixture is then cooled, concentrated, and partitioned between dichloromethane and aqueous sodium bicarbonate. The organic phase is separated and filtered through sodium sulfate and concentrated. The crude product is crystallized from dichloromethane and hexane to give the title compound, which is then recrystallized from ethyl ether/ethyl acetate/hexane, mp 202.0°-202.5°; MS (m/z) at 321; IR (mineral oil) 1674, 1639, 1501, 1358 and 1401 cm-1 ; NMR (CDCl3) 1.15, 2.18, 2.29, 5.32, 7.41, 7.62 and 8.15 δ.

Workup

  1. temperatureis heated at 80° for 45 min
  2. temperatureThe reaction mixture is then cooled
  3. concentrationconcentrated
  4. custompartitioned between dichloromethane and aqueous sodium bicarbonate
  5. customThe organic phase is separated
  6. filtrationfiltered through sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product is crystallized from dichloromethane and hexane

Sources & evidence

ORD record
ord-6fc1a62dc8244a97b07cd32f2cbd2e1e
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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