Hydrochloric Acid → HCID 59198862, compound

HRID 72736Notes

Reaction equation

HRID 72736 reaction equation
[CH:1]1([C:7]2[N:11]3[C:12]4[C:17]([NH:18][C:19](=[O:20])[C:10]3=[CH:9][N:8]=2)=[CH:16][CH:15]=[C:14](C(OCC)=O)[CH:13]=4)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Mg]Br.Cl.[C:30](=O)([O-])O.[Na+].C([O:37][CH2:38][CH3:39])C>O1CCCC1.O>[CH:1]1([C:7]2[N:11]3[C:12]4[C:17]([NH:18][C:19](=[O:20])[C:10]3=[CH:9][N:8]=2)=[CH:16][CH:15]=[C:14]([C:38]([OH:37])([CH3:39])[CH3:30])[CH:13]=4)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 59198728HCID 59198728, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59198862HCID 59198862, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-cyclohexyl-4-oxo-4,5-dihydroimidazo[1,5-a]-quinoxaline-8-carboxyate as synthesized in Example 102, 503 mg was suspended in 9 mL of tetrahydrofuran, and into the suspension 1.7 mL of 3M methylmagnesium bromide solution in diethyl ether was dropped, followed by 23 hours' stirring at room temperature under nitrogen atmosphere. The reaction liquid was poured into water, and of which pH was adjusted to 9 with diluted hydrochloric acid and saturated aqueous sodium hydrogencarbonate solution. The precipitated crystals were recovered by filtration and washed with water. The crude product was heat-suspended in acetone and purified. The crude product was alkali-treated and thereafter its pH was adjusted to 10 by addition of diluted hydrochoric acid (i.e. the carboxyic acid was dissolved in water). Thus precipitated crystals were recovered by filtration, washed with water, heat-suspended in 2-propanol and purified. Further recrystallizing the same from N,N-dimethylformamide-water mixed solvent, 133 mg of the title compound was obtained.

Workup

  1. customThe reaction liquid
  2. filtrationThe precipitated crystals were recovered by filtration
  3. washwashed with water
  4. custompurified
  5. additionThe crude product was alkali-treated
  6. additionits pH was adjusted to 10 by addition of diluted hydrochoric acid (i.e. the carboxyic acid
  7. dissolutionwas dissolved in water)
  8. filtrationThus precipitated crystals were recovered by filtration
  9. washwashed with water
  10. custompurified
  11. customFurther recrystallizing the same from N,N-dimethylformamide-water mixed solvent

Sources & evidence

ORD record
ord-5cbb02e84f934ca99ca0fa3b0d902eb7
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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