HCID 178499257, compound → HCID 178499317, compound

HRID 1694472Notes

Reaction equation

HRID 1694472 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7](Br)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:21][CH2:22][C@H:23]([OH:26])[CH2:24][CH2:25]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4]

Participants

4

Reactant 1

HCID 178499257HCID 178499257, compound

Product 1

HCID 178499317HCID 178499317, compoundYield 104.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methylcyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (229 mg, 0.50 mmol) in dry MeOH (5 mL) was added 10% palladium on charcoal (53 mg), nitrogen was bubbled through solution for 10 min, then it was displaced by hydrogen, and the mixture was stirred at room temperature for 24 h. The mixture was filtered through celite washing with MeOH, and filtrate was concentrated under reduced pressure to give 199 mg of crude 3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methylcyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester, which was used in the following step without purification.

Workup

  1. customwas bubbled through solution for 10 min
  2. filtrationThe mixture was filtered
  3. washthrough celite washing with MeOH, and filtrate
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-05df97fb37754cf8b1227eef72c0b46f
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

Loading…