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

HRID 2405869Notes

Reaction equation

HRID 2405869 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-f6247eb589854f4a98d7c799318ffde8
Source dataset
uspto-grants-2014_08
Patent number
US08809327B2

Reaction notes

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