Acetone → HCID 131729256, compound

HRID 554874Notes

Reaction equation

HRID 554874 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:17][CH2:16][C:15]4[N:18]=[C:19]([C:21]5[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=5)[S:20][C:14]=4[C:13]3=[O:28])=[CH:8][C:7]=2[O:29][CH3:30])[CH2:2]1.[CH3:31][C:32]([CH3:34])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[ClH:27].[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C:19]2[S:20][C:14]3[C:13](=[O:28])[N:12]([C:9]4[CH:10]=[CH:11][C:6]([O:5][CH:3]5[CH2:4][N:1]([CH:32]([CH3:34])[CH3:31])[CH2:2]5)=[C:7]([O:29][CH3:30])[CH:8]=4)[CH2:17][CH2:16][C:15]=3[N:18]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 249911625-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one

Product 1

HCID 131729256HCID 131729256, compoundYield 107.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Dissolve 5-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (1.0 g, 2.26 mmol) and acetone (250 μL, 3.39 mmol) in dry 1,2-dichloroethane. Add sodium triacetoxyborohydride (1.0 g, 4.53 mmol) and stir overnight at room temperature. Add 1 N NaOH solution to the reaction mixture and extract with CH2Cl2 (2×25 mL). Combine the organic portions and wash with water (2×25 mL). Dry the organic layer with Na2SO4, then filter, and concentrate in vacuo. Triturate the crude yellow solid with Et2O and filter. Wash the solid with Et2O several times and re-dissolve in CHCl3. Add 1 N HCl/Et2O solution (1.5 mL) and remove the solvent in vacuo to give 630 mg (53%) of the title compound. ES/MS m/z (35Cl) 484.2 [M+1]+.

Workup

  1. extractionextract with CH2Cl2 (2×25 mL)
  2. washCombine the organic portions and wash with water (2×25 mL)
  3. dry with materialDry the organic layer with Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customTriturate the crude yellow solid with Et2O
  7. filtrationfilter
  8. washWash the solid with Et2O several times
  9. dissolutionre-dissolve in CHCl3
  10. additionAdd 1 N HCl/Et2O solution (1.5 mL)
  11. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-aefc49f2ac1841d9becd76dc196ca1b5
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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