Methanol → HCID 67004793, compound

HRID 1513980Notes

Reaction equation

HRID 1513980 reaction equation
[C:1]([O:5][C:6](=[O:50])[NH:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:25]CC3C=CC=CC=3)[CH:21]=2)[C:16]=1[C:33](=[O:49])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:36][CH:35]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+].CO>[Pd].C(O)C>[C:1]([O:5][C:6](=[O:50])[NH:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([OH:25])[CH:21]=2)[C:16]=1[C:33](=[O:49])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:36][CH:35]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 11158169HCID 11158169, compound

Product 1

HCID 67004793HCID 67004793, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a round bottom flask add (2-{6-benzyloxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl}-5-fluoro-phenyl)-carbamic acid tert-butyl ester (0.075 g, 0.11 mmol), ammonium formate (0.056 g, 0.89 mmol), methanol (5 mL) and a slurry of 10% Pd/C (0.012 g, ˜15% by weight) and ethanol (2 mL). Heat the mixture, with stirring, at reflux for 30 minutes. Cool the reaction to ambient temperature and filter it through a pad of Celite, then rinse the Celite with hot methanol. Evaporate the filtrate in vacuo and purify the resulting residue by radial chromatography over silica (4-9% MeOH gradient in CH2Cl2) to provide the product 61 mg (94%): mass spectrum (ion spray) m/z=585 (M+H).

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 30 minutes
  3. temperatureCool
  4. customthe reaction to ambient temperature
  5. filtrationfilter it through a pad of Celite
  6. washrinse the Celite with hot methanol
  7. customEvaporate the filtrate in vacuo
  8. custompurify the resulting residue by radial chromatography over silica (4-9% MeOH gradient in CH2Cl2)

Sources & evidence

ORD record
ord-5bd5b783c61e4229bb428c2c7ca3a6dd
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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