HCID 22293389, compound → HCID 22293422, compound

HRID 351476Notes

Reaction equation

HRID 351476 reaction equation
[CH2:1]([C:8]12[C:16](=[O:17])[N:15]([CH3:18])[CH2:14][CH:13]1[CH2:12][CH2:11][N:10](CC1C=CC=CC=1)[CH2:9]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)(=O)C.[Pd].O>[CH2:1]([C:8]12[C:16](=[O:17])[N:15]([CH3:18])[CH2:14][CH:13]1[CH2:12][CH2:11][NH:10][CH2:9]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 22293389HCID 22293389, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22293422HCID 22293422, compoundYield 0.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of the compound of Example 200, Step D (0.034 g, 10.10 mmol) in acetic acid (18 mL) was added slurry of palladium on carbon (10% by weight, 0.030 g) in H2O (2 mL). The reaction mixture was shaken under 50 psig hydrogen for 24 h, an additional aliquot of palladium on carbon (0.030 g) was introduced and the reaction was continued under 50 psig hydrogen for another 24 h. The reaction mixture was filtered through a bed of Celite® with the aid of MeOH, concentrated under vacuum, and the residue was partitioned between CH2Cl2 and H2O at pH 9. The organic layer was removed and the aqueous layer was washed twice with CH2Cl2, the organic layers were combined and washed with a saturated aqueous brine solution, dried over Na2SO4, filtered and concentrated under vacuum. Purification by silica gel chromatography employing 3% MeOH/0.2% NH4OH/CH2Cl2 as the eluant afforded the compound of Example 200, Step E (0.019 g): +APcl MS (M+1)+245; 1H NMR (400 MHz, CDCl3) δ: 7.10-7.24 (arom, series of m, 5 H), 3.21 (m, 1H), 2.71 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a bed of Celite® with the aid of MeOH
  2. concentrationconcentrated under vacuum
  3. customthe residue was partitioned between CH2Cl2 and H2O at pH 9
  4. customThe organic layer was removed
  5. washthe aqueous layer was washed twice with CH2Cl2
  6. washwashed with a saturated aqueous brine solution
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-e1a95bdc338749dab9f085465fe52e6f
Source dataset
uspto-grants-2004_06
Patent number
USRE038524E1

Reaction notes

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