HCID 86717463, compound → HCID 86717464, compound

HRID 712004Notes

Reaction equation

HRID 712004 reaction equation
[C:1]([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:3])[CH3:2]>[Pd].CO>[C:1]([O:4][CH2:5][CH:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]2[C:18]([NH2:19])=[CH:17][N:16]=[C:15]3[CH:22]=[CH:23][S:24][C:14]=23)[CH2:8][O:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86717463HCID 86717463, compound

Product 1

HCID 86717464HCID 86717464, compoundYield 75.2%

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 (210 mg, 0.600 mmol) and 10% palladium on carbon (0.21 g) in methanol (4.0 mL) was subjected to balloon pressure of H2 at room temperature for 2 h. The mixture was filtered, and the filtrate was concentrated and purified with flash chromatography (eluting with 15% methanol in dichloromethane) to give the desired product (145 mg, 75%). LCMS calculated for C15H20N3O3S (M+H)+: m/z=322.1. Found: 322.0.

Workup

  1. customat room temperature
  2. customfor 2 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified with flash chromatography (eluting with 15% methanol in dichloromethane)

Sources & evidence

ORD record
ord-36929a14d65b4770aade73b25b66c037
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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