Hydrochloride methanol → HCID 25190128, compound

HRID 1692438Notes

Reaction equation

HRID 1692438 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]1[C:17]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:22][CH2:21]2)=[O:19])=[C:16]([CH3:31])[CH:15]=[C:14]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=2)[N:13]=1)C1C=CC=CC=1.Cl.CO>CO.[Pd]>[OH:8][CH2:9][CH2:10][O:11][C:12]1[C:17]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:22][CH2:21]2)=[O:19])=[C:16]([CH3:31])[CH:15]=[C:14]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:39])([F:41])[F:40])[CH:33]=2)[N:13]=1

Participants

5

Reactant 2

HCID 21893726Hydrochloride methanolHCID 57580539HCID 57580539, compound

Product 1

HCID 25190128HCID 25190128, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.22 g (0.4 mmol) of [2-(2-benzyloxy-ethoxy)-4-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 52) in 10 ml of MeOH was treated with 0.04 g (0.04 mmol) of Pd—C (10%) and 0.5 ml of HCl/MeOH (1 molar). The reaction mixture was hydrogenated at RT and ambient pressure until the absorption of H2 stopped (1 hour). After filtration with the aid of Dicalite, the filtrate was poured into crashed ice, the pH was adjusted to 8-9 with the help of sodium carbonate solution and the reaction mixture was extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography [CH2Cl2 (sat. with NH3)/MeOH 98:2 to 4:1] to give 0.16 g (86%) of the title compound as colorless oil. MS: 478.2 (MH+).

Workup

  1. customwas hydrogenated at RT
  2. customambient pressure until the absorption of H2
  3. custom(1 hour)
  4. filtrationAfter filtration with the aid of Dicalite
  5. additionthe filtrate was poured
  6. extractionthe reaction mixture was extracted twice with CH2Cl2
  7. washthe organic phases were washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by flash column chromatography [CH2Cl2 (sat. with NH3)/MeOH 98:2 to 4:1]

Sources & evidence

ORD record
ord-690d0c8c9cd74bf589f5cec448d1f3e9
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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