Sodium Bicarbonate → Methyl 4-(4-{[(3-cyano-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)sulfanyl]methyl}-1,3-thiazol-2-yl)benzoate

HRID 1916274Notes

Reaction equation

HRID 1916274 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[S:6][CH:7]=1.C(=O)(O)[O-].[Na+].[C:23]([C:25]1[C:26]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:27]2[CH2:34][CH2:33][CH2:32][C:28]2=[N:29][C:30]=1[S-:31])#[N:24].[Na+]>O>[C:23]([C:25]1[C:26]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:27]2[CH2:34][CH2:33][CH2:32][C:28]2=[N:29][C:30]=1[S:31][CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[S:6][CH:7]=1)#[N:24]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 45156786Methyl 4-[4-(chloromethyl)-1,3-thiazol-2-yl]benzoateHCID 66932949Sodium [3-cyano-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridine-2-thiolate]

Product 1

HCID 44133054Methyl 4-(4-{[(3-cyano-4-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)sulfanyl]methyl}-1,3-thiazol-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

315 mg (1.18 mmol) of methyl 4-[4-(chloromethyl)-1,3-thiazol-2-yl]benzoate (prepared as described in WO 2005/011685) and 329 mg (3.92 mmol) of sodium bicarbonate are added to the reaction mixture from Example 18A, and the mixture is stirred at RT for 16 h. 50 ml of water were added, and the reaction was extracted with ethyl acetate. The organic phase was washed with water and a saturated aqueous sodium chloride solution, dried over magnesium sulfate and freed from the solvent on a rotary evaporator. The residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. extractionthe reaction was extracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
  4. customfreed from the solvent on a rotary evaporator
  5. customThe residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-015d5404084443ecad8826b73ed9bda9
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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