HCID 178511085, compound → HCID 178511084, compound

HRID 711935Notes

Reaction equation

HRID 711935 reaction equation
[N+:1]([C:4]1[C:5]([NH:13][C@H:14]2[CH2:19][CH2:18][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[CH2:15][CH2:16][C@H:17]([CH2:20][C:21]#[N:22])[CH2:18][CH2:19]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 178511085HCID 178511085, compound

Product 1

HCID 178511084HCID 178511084, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of {trans-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acetonitrile (0.16 g, 0.50 mmol) and 10% palladium on carbon (20 mg) in methanol (5 mL) was hydrogenated under balloon pressure of H2 at room temperature for 2 h. The reaction mixture was filtered and the filtrate concentrated to give the desired product (0.124 g, 86%), which was used directly in the next step. LCMS calculated for C15H19N4S (M+H)+: m/z=287.1. Found: 287.1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-ed96486527c54418b7ec6d429202292a
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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