Sodium borohydride → HCID 10015041, compound

HRID 1063115Notes

Reaction equation

HRID 1063115 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[S:13][C:14]([C:17]([NH2:19])=[O:18])=[C:15]([NH2:16])[C:7]=12)(=[O:5])[CH3:4]>CO>[NH2:16][C:15]1[C:7]2[C:8](=[N:9][C:10]([CH3:12])=[CH:11][C:6]=2[CH:3]([OH:5])[CH3:4])[S:13][C:14]=1[C:17]([NH2:19])=[O:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23400900HCID 23400900, compound

Product 1

HCID 10015041HCID 10015041, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A spatula tip full of NaBH4 was added to a solution of 9.9 mg 4-acetyl-3-amino-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide in 1 mL MeOH. After 0.5 h, the reaction was concentrated in vacuo, quenched with aqueous NH4Cl, extracted 4 times into EtOAc, concentrated in vacuo, dissolved in MeOH—CH2Cl2, filtered, concentrated and dried in vacuo at 60° C. to provide 8.1 mg of the title compound as a beige solid.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customquenched with aqueous NH4Cl
  3. extractionextracted 4 times into EtOAc
  4. concentrationconcentrated in vacuo
  5. dissolutiondissolved in MeOH—CH2Cl2
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-88c198bf0e6448e1a80fe4af13200e63
Source dataset
uspto-grants-2005_11
Patent number
US06964956B2

Reaction notes

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