Sodium Bicarbonate → HCID 67197212, compound

HRID 550802Notes

Reaction equation

HRID 550802 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:20]3[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]3)[C:12]3[CH2:17][S:16](=[O:19])(=[O:18])[CH2:15][C:13]=3[N:14]=2)=[C:4]([F:27])[CH:3]=1.[NH2:28]C(O)C.[C:32]([O:35][BH-](OC(=O)C)OC(=O)C)(=O)[CH3:33].[Na+].C(=O)(O)[O-].[Na+].[ClH:51].O1CCOCC1>C(O)(=O)C.C1COCC1.CO.C(Cl)Cl>[ClH:1].[ClH:51].[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[N:10]=[C:11]([N:20]3[CH2:21][CH2:22][CH:23]([NH:28][CH2:33][CH2:32][OH:35])[CH2:24][CH2:25]3)[C:12]3[CH2:17][S:16](=[O:18])(=[O:19])[CH2:15][C:13]=3[N:14]=2)=[C:4]([F:27])[CH:3]=1

Participants

9

Reactant 5

HCID 516892Sodium BicarbonateHCID 522583Acetaldehyde ammoniaHCID 5049666Sodium triacetoxyborohydrideHCID 204431481,4-Dioxane hydrochlorideHCID 67197393HCID 67197393, compound

Product 1

HCID 67197212HCID 67197212, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 400 mg of 1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-one, 10 ml of methylene chloride, 65 μl of aminoethanol, and two drops of acetic acid was stirred at ambient temperature for 1 hour, here was then added 617 mg of sodium triacetoxyborohydride, and the mixture was stirred at ambient temperature for 3 hours. Saturated aqueous sodium bicarbonate was added to the reaction mixture, and the resultant mixture was extracted with chloroform-THF mixed solvent. The organic phase obtained was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was dissolved in THF-MeOH, here was added 4M HCl-dioxane solution, the solution was concentrated under reduced pressure, and the residue was recrystallized from EtOH-acetonitrile to yield 426 mg of 2-({1-[2-(4-chloro-2,5-difluorophenyl)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperidin-4-yl}amino)ethanol dihydrochloride.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 3 hours
  2. extractionthe resultant mixture was extracted with chloroform-THF mixed solvent
  3. customThe organic phase obtained
  4. washwas washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue obtained
  8. concentrationthe solution was concentrated under reduced pressure
  9. customthe residue was recrystallized from EtOH-acetonitrile

Sources & evidence

ORD record
ord-332f0010d3084ac49e14a895a2d7abe6
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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