Ammonium formate → HCID 57709157, compound

HRID 547062Notes

Reaction equation

HRID 547062 reaction equation
C([O-])=O.[NH4+].[CH2:5]([C:7]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:33]=[C:34]([CH2:38][C:39]([OH:41])=[O:40])[CH:35]=[N:36][CH:37]=2)=[C:28]([CH3:42])[CH:27]=1)([C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]2([OH:24])[CH2:23][CH2:22][S:21][CH2:20][CH2:19]2)=[C:12]([CH3:25])[CH:11]=1)[CH2:8][CH3:9])[CH3:6]>C(O)C.[Pd]>[CH2:5]([C:7]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:33]=[C:34]([CH2:38][C:39]([OH:41])=[O:40])[CH:35]=[N:36][CH:37]=2)=[C:28]([CH3:42])[CH:27]=1)([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]2([OH:24])[CH2:19][CH2:20][S:21][CH2:22][CH2:23]2)=[C:12]([CH3:25])[CH:11]=1)[CH2:8][CH3:9])[CH3:6]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57709144HCID 57709144, compound

Product 1

HCID 57709157HCID 57709157, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

Ammonium formate (100 mg, 1.6 mmol) and Pd/C (30 mg) were added to a solution of [5-(4-{1-ethyl-1-[4-(4-hydroxy-tetrahydrothiopyran-4-ylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic acid (Example 137-(3); 5 mg, 0.01 mmol) in ethanol, and the mixture was stirred with microwave heating at 130° C. for 10 minutes. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (dichloromethane/methanol=10/1) to give the title compound (3.5 mg, 70%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by thin layer silica gel chromatography (dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-5afce23576ea42778314246a95504c5c
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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