HCID 86717463, compound → HCID 86717520, compound

HRID 712060Notes

Reaction equation

HRID 712060 reaction equation
C([O:4][CH2:5][CH:6]1[CH:11]=[CH:10][C@H:9]([NH:12][C:13]2[C:18]([N+:19]([O-])=O)=[CH:17][N:16]=[C:15]3[CH:22]=[CH:23][S:24][C:14]=23)[CH2:8][O:7]1)(=O)C>[Pd].CO>[NH2:19][C:18]1[C:13]([NH:12][C@@H:9]2[CH2:8][O:7][C@@H:6]([CH2:5][OH:4])[CH2:11][CH2:10]2)=[C:14]2[S:24][CH:23]=[CH:22][C:15]2=[N:16][CH:17]=1

Participants

4

Reactant 1

HCID 86717463HCID 86717463, compound

Product 1

HCID 86717520HCID 86717520, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of {(5S)-5-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]-5,6-dihydro-2H-pyran-2-yl}methyl acetate (366 mg, 1.05 mmol) and 10% palladium on carbon (0.18 g) in methanol (7.0 mL) was subjected to balloon pressure of H2 at room temperature for 2 h. The mixture was filtered and treated with 1 M NaOH (1 mL) for 1 h. The mixture was diluted with methanol and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give two peaks in 5:1 ratio. The major peak is the title compound (154 mg, 58%). LCMS calculated for C13H18N3O2S (M+H)+: m/z=280.1. Found: 280.1.

Workup

  1. customat room temperature
  2. customfor 2 h
  3. filtrationThe mixture was filtered
  4. additiontreated with 1 M NaOH (1 mL) for 1 h
  5. additionThe mixture was diluted with methanol
  6. custompurified with prep-LCMS (XBridge C18 column
  7. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)
  8. customto give two peaks in 5:1 ratio

Sources & evidence

ORD record
ord-f5e02392a86846bd89a35896a10bdebb
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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