HCID 178511085, compound → HCID 178511084, compound

HRID 711974Notes

Reaction equation

HRID 711974 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, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of {trans-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acetonitrile (1.0 g, 3.2 mmol) and 10% palladium on carbon (0.3 g, 0.3 mmol) in methanol (30 mL) was hydrogenated under balloon pressure of H2 at room temperature for 5 h. The reaction mixture was filtered. The filtrate was concentrated, diluted with dichlormethane, dried over MgSO4, and concentrated. The residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product. (0.63 g, 70%). LCMS calculated for C15H19N4S (M+H)+: m/z=287.1. Found: 287.1.

Workup

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

Sources & evidence

ORD record
ord-8fbf60be53ea4d36a17e2e607269a957
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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