Ammonium formate → HCID 59751420, compound

HRID 732795Notes

Reaction equation

HRID 732795 reaction equation
[CH3:1][C:2]([CH3:49])([CH3:48])[CH2:3][O:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24]CC4C=CC=CC=4)[CH:20]=3)[C:15]=2[O:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][N:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[CH:35][CH:34]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6].C([O-])=O.[NH4+]>[Pd].CO>[CH3:1][C:2]([CH3:49])([CH3:48])[CH2:3][O:4][S:5]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[CH:20]=3)[C:15]=2[O:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][N:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[CH:35][CH:34]=2)=[CH:12][CH:13]=1)(=[O:6])=[O:7]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59751426HCID 59751426, compound

Product 1

HCID 59751420HCID 59751420, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a round bottom flask add the product from Example 66 (42 mg, 0.062 mmol), ammonium formate (29 mg, 0.464 mmol), 10% Pd/C (6 mg, ˜15% by weight) and MeOH (5 mL). Heat the mixture at reflux for 35 minutes. Cool the reaction to ambient temperature and filter it through a pad of Celite, then rinse the Celite with hot ethyl acetate and hot methanol. Evaporate the filtrate in vacuo and purify the resulting residue by radial chromatography over silica (2-5% MeOH gradient in CH2Cl2) to provide 27 mg of 4-{6-hydroxy-1-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl}-benzenesulfonic acid 2,2-dimethyl-propyl ester (74%). Dissolve the free base (6.7 mg) in CH2Cl2 (3 mL) and add 0.023 mL (2 equivalents (eq.)) of a 1.0M solution of hydrochloric acid in diethyl ether. Shake this solution for 1-2 minutes at ambient temperature and evaporate it in vacuo to provide 7.1 mg of the title compound. MS (IS+) m/e 590 (M+1−HCl).

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 35 minutes
  3. temperatureCool
  4. customthe reaction to ambient temperature
  5. filtrationfilter it through a pad of Celite
  6. washrinse the Celite with hot ethyl acetate and hot methanol
  7. customEvaporate the filtrate in vacuo
  8. custompurify the resulting residue by radial chromatography over silica (2-5% MeOH gradient in CH2Cl2)

Sources & evidence

ORD record
ord-b9a984152b3247cf8ec819a8f23674c3
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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