Formaldehyde → HCID 44207427, compound

HRID 1677374Notes

Reaction equation

HRID 1677374 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:3]1.[BH3-][C:30]#N.[Na+].C=O>CO.CC(O)=O>[CH3:30][N:2]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:3]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67344036HCID 67344036, compound

Product 1

HCID 44207427HCID 44207427, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent2×

Procedure

To a mixture of 2-(3,4-dimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid pyrrolidin-3-ylamide hydrochloride (12 mg, 0.03 mmol) in MeOH (0.5 mL) was added NaBH3CN (15 mg, 0.23 mmol). A solution of HOAc (1 drop) in MeOH (1 mL) was prepared and 2 drops of this solution was added to the reaction mixture so that the pH ˜4. Aqueous CH2O (37%, 25 μL, 0.34 mmol) was added to the reaction mixture which was then stirred at room temperature for 2 h, partitioned between saturated Na2CO3 and CH2Cl2. The aqueous layer was extracted with CH2Cl2 and the combined organic phases were dried (Na2SO4) and concentrated to give a pale yellow solid. The crude product was washed with Et2O to afford 11 mg (100%) of 2-(3,4-dimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methyl-pyrrolidin-3-yl)-amide as a yellow powder. MP 193-194° C., M+H 382.

Workup

  1. custompartitioned between saturated Na2CO3 and CH2Cl2
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated
  5. customto give a pale yellow solid
  6. washThe crude product was washed with Et2O

Sources & evidence

ORD record
ord-559e8c0d3809450bba6eb4cf59200b5d
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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