3-{3-[(6-Nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acrylonitrile → 3-{3-[(6-Aminothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}propanenitrile

HRID 712040Notes

Reaction equation

HRID 712040 reaction equation
[N+:1]([C:4]1[C:5]([NH:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH:16]([CH:20]=[CH:21][C:22]#[N:23])[CH2:15]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[C:5]([NH:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][CH2:21][C:22]#[N:23])[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 867174943-{3-[(6-Nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acrylonitrile

Product 1

HCID 867174953-{3-[(6-Aminothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}propanenitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-{3-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acrylonitrile (0.13 g, 0.40 mmol) and 10% Pd/C (0.05 g) in methanol (10 mL) was hydrogenated under balloon pressure of H2 at room temperature over weekend. The mixture was filtered, concentrated and purified on silica gel column (eluting with 0-10% MeOH in methylene chloride) to give the desired product. LCMS calculated for C16H21N4S (M+H)+: m/z=301.1. Found: 301.0.

Workup

  1. waitwas hydrogenated under balloon pressure of H2 at room temperature over weekend
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. custompurified on silica gel column (eluting with 0-10% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-1cd4e85cb146446ba711f4368b7f1402
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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