HCID 86717476, compound → HCID 86717477, compound

HRID 712019Notes

Reaction equation

HRID 712019 reaction equation
[OH:1][C:2]1([CH2:21][C:22]#[N:23])[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][N:12]=[C:11]3[CH:18]=[CH:19][S:20][C:10]=23)[CH2:4][CH2:3]1>CO.[Pd]>[NH2:15][C:14]1[C:9]([NH:8][CH:5]2[CH2:6][CH2:7][C:2]([CH2:21][C:22]#[N:23])([OH:1])[CH2:3][CH2:4]2)=[C:10]2[S:20][CH:19]=[CH:18][C:11]2=[N:12][CH:13]=1

Participants

4

Reactant 1

HCID 86717476HCID 86717476, compound

Product 1

HCID 86717477HCID 86717477, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of {1-hydroxy-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acetonitrile (0.11 g, 0.33 mmol) and 10% Pd/C (0.050 g) in methanol (7 mL) was hydrogenated under balloon pressure of H2 at room temperature for 2 h. The mixture was filtered, concentrated and purified on silica gel column (eluting with 0-10% MeOH in methylene chloride) to give the desired product as a mixture of cis- and trans-isomer mixtures (38 mg, 38%). LCMS calculated for C15H19N4OS (M+H)+: m/z=303.1. Found: 303.0.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified on silica gel column (eluting with 0-10% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-12109d8b83674756b5548058a3dbab9b
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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