HCID 86717445, compound → HCID 86717446, compound

HRID 711982Notes

Reaction equation

HRID 711982 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][N:11]=[C:10]3[CH:17]=[CH:18][S:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([NH:7][C:8]2[C:13]([NH2:14])=[CH:12][N:11]=[C:10]3[CH:17]=[CH:18][S:19][C:9]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 86717445HCID 86717445, compound

Product 1

HCID 86717446HCID 86717446, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-cyclohexyl-6-nitrothieno[3,2-b]pyridin-7-amine (0.065 g, 0.23 mmol) and 10% palladium on carbon (0.02 g) in methanol (3 mL) was hydrogenated under balloon pressure of H2 at room temperature for 1 h. The reaction mixture was filtered. The filtrate was concentrated, diluted with dichloromethane, dried over MgSO4, and concentrated. The residue was purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane) to give the desired product (42 mg, 72%). LCMS calculated for C13H18N3S (M+H)+: m/z=248.1. Found: 248.1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with dichloromethane
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-9dbad2de56bf442d8f13add1b9ff02e5
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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