HCID 86717568, compound → HCID 86717567, compound

HRID 712116Notes

Reaction equation

HRID 712116 reaction equation
[N+:1]([C:4]1[C:5]([NH:13][C@@H:14]2[CH2:19][O:18][C@@H:17]([CH2:20][C:21]#[N:22])[CH2:16][CH2:15]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[C:5]([NH:13][C@@H:14]2[CH2:19][O:18][C@@H:17]([CH2:20][C:21]#[N:22])[CH2:16][CH2:15]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 86717568HCID 86717568, compound

Product 1

HCID 86717567HCID 86717567, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

{(2R,5S)-5-[(6-Nitrothieno[3,2-b]pyridin-7-yl)amino]tetrahydro-2H-pyran-2-yl}acetonitrile (712 mg, 2.24 mmol) (first fraction from last step) and 10% palladium on carbon (360 mg) in methanol (15 mL) was subjected to balloon pressure of H2 at room temperature for 2 h. The reaction mixture was filtered and concentrated and purified with flash chromatography (15% methanol/dichloromethane) to give the desired product (604 mg, 94%). LCMS calculated for C14H17N4OS (M+H)+: m/z=289.1. Found: 289.0.

Workup

  1. customat room temperature
  2. customfor 2 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. custompurified with flash chromatography (15% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a4ff35c0dcf14074a870432070ba464b
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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