Ammonium Chloride → HCID 10331631, compound

HRID 1063116Notes

Reaction equation

HRID 1063116 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1[C:16]2[C:11](=[N:12][C:13]([CH3:20])=[CH:14][C:15]=2[CH:17]([OH:19])C)[S:10][C:9]=1[C:21]([NH2:23])=[O:22].[NH4+].[Cl-]>C1COCC1>[NH2:7][C:8]1[C:16]2[C:11](=[N:12][C:13]([CH3:20])=[CH:14][C:15]=2[CH:17]=[O:19])[S:10][C:9]=1[C:21]([NH2:23])=[O:22]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10015041HCID 10015041, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10331631HCID 10331631, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (0.31 g) was added to a suspension of 0.60 g of 3-amino-6-methyl-thieno[2,3-b]pyridine-2,4-dicarboxylic acid 2-amide 4-(methoxy-methyl-amide) (see Example 15) in 15 mL dry THF at −10° C. and stirred 1 h under Ar. Aqueous NH4Cl was added slowly and the mixture was filtered through diatomaceous earth, washing with H2O and EtOAc. The aqueous phase was separated and extracted 3 times with more with EtOAc and the combined organics were and concentrated in vacuo to a resin that was flashed chromatographed eluting with 30% acetone-petroleum ether to afford 163 mg 3-amino-4-formyl-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide as a dark resin.

Workup

  1. filtrationthe mixture was filtered through diatomaceous earth
  2. washwashing with H2O and EtOAc
  3. customThe aqueous phase was separated
  4. extractionextracted 3 times with more with EtOAc
  5. concentrationconcentrated in vacuo to a resin that
  6. customwas flashed chromatographed
  7. washeluting with 30% acetone-petroleum ether

Sources & evidence

ORD record
ord-f950e7c7d38c43d29e568079708eab49
Source dataset
uspto-grants-2005_11
Patent number
US06964956B2

Reaction notes

Loading…