HCID 178526780, compound → HCID 178508004, compound

HRID 711977Notes

Reaction equation

HRID 711977 reaction equation
[N+:1]([C:4]1[C:5]([NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([CH2:20][OH:21])[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][OH:21])[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 178526780HCID 178526780, compound

Product 1

HCID 178508004HCID 178508004, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of {trans-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}methanol (0.080 g, 0.26 mmol) (Example 2, Step 1) and 10% palladium on carbon (0.03 g) in methanol (3 mL) was hydrogenated under balloon pressure of H2 at room temperature for 1 h. The mixture was filtered. The filtrate was concentrated, diluted with dichloromethane, then dried over MgSO4, and concentrated. The residue was purified on silica gel (eluting with 10% MeOH in dichloromethane) to give the desired product (41 mg, 57%). LCMS calculated for C14H20N3OS (M+H)+: m/z=278.1. Found: 278.1.

Workup

  1. filtrationThe 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 10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-425e8828c23447aabe2442bcd0b3cfd8
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…