Acetic Acid → HCID 68642064, compound

HRID 1498964Notes

Reaction equation

HRID 1498964 reaction equation
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[C:7]3[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:8]=3[N:9]=[C:2]12.[C:19](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH3:19][N:6]1[CH2:5][CH2:4][N:3]2[C:7]3[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:8]=3[N:9]=[C:2]2[CH2:1]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68641311HCID 68641311, compound

Product 1

HCID 68642064HCID 68642064, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (0.98 g, 4.00 mmol) prepared in the Step 38-1-5 was dissolved in methanol (100 ml), and acetic acid (1.00 ml) and a 37% formaldehyde aqueous solution (1.2 ml) were added thereto. Thereafter, sodium cyanoborohydride (0.57 g, 9.07 mmol) was added to the mixture, and the resulting mixture was stirred. After 30 minutes, the mixture was concentrated under a reduced pressure. Chloroform was added to the concentrate, and the resulting mixture was washed with a saturated sodium bicarbonate solution. The washed product was dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (958 mg, 92%) as a light-brown powder.

Workup

  1. concentrationthe mixture was concentrated under a reduced pressure
  2. additionChloroform was added to the concentrate
  3. washthe resulting mixture was washed with a saturated sodium bicarbonate solution
  4. dry with materialThe washed product was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-b21e43e4a79e44a7969166eff83e721a
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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