HCID 66906974, compound → Thieno[3,2-b]pyridin-2-ylamine hydrochloride

HRID 1691552Notes

Reaction equation

HRID 1691552 reaction equation
[ClH:1].Br[C:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[S:5][C:4]=1[NH2:12]>CO.[Pd]>[ClH:1].[S:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:3]=[C:4]1[NH2:12]

Participants

4

Reactant 1

HCID 66906974HCID 66906974, compound

Product 1

HCID 66907303Thieno[3,2-b]pyridin-2-ylamine hydrochlorideYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of compound 145-H, (1.86 g, 6.16 mmol) and 10% Pd/C (0.49 g, 26.3% w/w) in methanol (75 mL) was catalytically hydrogenated on a Parr shaker at 25 psi. After 3 h, the catalyst was filtered, the reaction mixture recharged with 10% Pd/C (0.49 g, 26.3% w/w) and shaken an additional 16 h at 22 psi H2. The reaction was filtered, recharged with 10% Pd/C (0.20 g, 10.8% w/w), and shaken at 20 psi H2 for an additional 24 h. The reaction mixture was filtered, evaporated, and the free base isolated by washing with aqueous sodium bicarbonate. The resultant residue was purified by flash column chromatography (SiO2), eluting with 3% MeOH/CH2Cl2 to afford compound 146-A as a yellow solid (0.65 g, 57%). 1H-NMR (DMSO-d6): δ 6.4 (s, 1H), 7.1 (dd, 1H), 8.3 (2, 1H), 8.4 (s, 2H), 8.5 (d, 1H), 15.2 (br s, 1H); MS: m/z 151.1 (MH+).

Workup

  1. filtrationthe catalyst was filtered
  2. filtrationThe reaction was filtered
  3. stirringshaken at 20 psi H2 for an additional 24 h
  4. filtrationThe reaction mixture was filtered
  5. customevaporated
  6. customthe free base isolated
  7. washby washing with aqueous sodium bicarbonate
  8. customThe resultant residue was purified by flash column chromatography (SiO2)
  9. washeluting with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a08559d0b57c427ca69356fe59e82c7b
Source dataset
uspto-grants-2012_04
Patent number
US08153682B2

Reaction notes

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