{(1R,3S)-3-[(6-Nitrothieno[3,2-b]pyridin-7-yl)amino]cyclopentyl}acetonitrile → {(1R,3S)-3-[(6-Aminothieno[3,2-b]pyridin-7-yl)amino]cyclopentyl}acetonitrile

HRID 712083Notes

Reaction equation

HRID 712083 reaction equation
[N+:1]([C:4]1[C:5]([NH:13][C@H:14]2[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]#[N:21])[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[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]#[N:21])[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 86717538{(1R,3S)-3-[(6-Nitrothieno[3,2-b]pyridin-7-yl)amino]cyclopentyl}acetonitrile

Product 1

HCID 86717539{(1R,3S)-3-[(6-Aminothieno[3,2-b]pyridin-7-yl)amino]cyclopentyl}acetonitrileYield 85.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of {(1R,3S)-3-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclopentyl}acetonitrile (8 mg, 0.03 mmol) and 10% palladium on carbon (4 mg) in methanol (0.3 mL) was stirred under an atmosphere of H2 (balloon) overnight. The mixture was filtered and concentrated to give 7 mg of the desired product. LCMS calculated for C14H17N4S (M+H)+: m/z=273.1. Found: 273.0.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4aac38411711465ca5c42645b6c8d079
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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