Sodium hydride → HCID 86619736, compound

HRID 1921204Notes

Reaction equation

HRID 1921204 reaction equation
[H-].[Na+].Br[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[S:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[NH:20][C:19]2=[O:27])[CH2:14][CH2:13]1>CN(C=O)C>[O:27]=[C:19]1[N:20]([CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:18]1[CH:15]1[CH2:16][CH2:17][S:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 67336664HCID 67336664, compound

Product 1

HCID 86619736HCID 86619736, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (68.3 mg of a 60% dispersion in mineral oil, 1.71 mmol) followed by tert-butyl bromoacetate (0.189 mL, 1.28 mmol) was added to a solution of 1-tetrahydro-2H-thiopyran-4-yl-1,3-dihydro-2H-benzimidazol-2-one from Step B (200 mg, 0.854 mmol) in DMF (5 mL). After 1 h, the reaction was quenched with H2O (10 mL) and extracted with CH2Cl2 (10 mL). The organic layer was washed with saturated NaHCO3 (5 mL), dried over MgSO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 50:50, gave the title compound. MS: m/z=349 (M+1).

Workup

  1. customthe reaction was quenched with H2O (10 mL)
  2. extractionextracted with CH2Cl2 (10 mL)
  3. washThe organic layer was washed with saturated NaHCO3 (5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography
  8. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-7bf23c4841044535be6b418bf792e291
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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