HCID 178418361, compound → HCID 178453639, compound

HRID 712126Notes

Reaction equation

HRID 712126 reaction equation
[N+:1]([C:4]1[C:5]([NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:16][CH2:15]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[C:5]([NH:13][C@H:14]2[CH2:15][CH2:16][C@H:17]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:18][CH2:19]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178453640HCID 178453640, compound

Product 1

HCID 178453639HCID 178453639, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl ({trans-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}methyl)carbamate (0.32 g, 0.79 mmol) and 10% palladium on carbon (0.01 g) in methanol (3 mL) was hydrogenated under balloon pressure of hydrogen at room temperature for 2 h. The mixture was filtered and concentrated to give the desired product (0.3 g, 100%) to be used in the next step directly. LCMS calculated for C19H29N4O2S (M+H)+: m/z=377.2. Found: 377.1.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6b6c9638134c4257a8c5abf3f39f0a7c
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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