N-[(2S)-Bicyclo[2.2.1]hept-2-yl]-6-nitrothieno[3,2-b]pyridin-7-amine → N7-[(2S)-Bicyclo[2.2.1]hept-2-yl]thieno[3,2-b]pyridine-6,7-diamine

HRID 712009Notes

Reaction equation

HRID 712009 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][N:12]=[C:11]2[CH:18]=[CH:19][S:20][C:10]=12>[Pd].CO>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[C:14]([NH2:15])=[CH:13][N:12]=[C:11]2[CH:18]=[CH:19][S:20][C:10]=12

Participants

4

Reactant 1

HCID 86717467N-[(2S)-Bicyclo[2.2.1]hept-2-yl]-6-nitrothieno[3,2-b]pyridin-7-amine

Product 1

HCID 86717468N7-[(2S)-Bicyclo[2.2.1]hept-2-yl]thieno[3,2-b]pyridine-6,7-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[(2S)-bicyclo[2.2.1]hept-2-yl]-6-nitrothieno[3,2-b]pyridin-7-amine (0.080 g, 0.28 mmol) and 10% palladium on carbon (0.03 g) in methanol (3 mL) was subjected to balloon pressure of H2 at room temperature for 1 h. The mixture was filtered and the filtrate concentrated to give the desired product, which was used directly in the next step without further purification. LCMS calculated for C14H18N3S (M+H)+: m/z=260.1. Found: 260.0.

Workup

  1. customat room temperature
  2. customfor 1 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-89112b425a6e432f9877967a56ddca4b
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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