Sodium hydride → HCID 178495763, compound

HRID 1470012Notes

Reaction equation

HRID 1470012 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH:7][C:8]([C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]4)[CH2:11]2)[CH2:17]3)=[O:9])=[N:4][CH:3]=1.Br[CH2:21][CH2:22][O:23][CH3:24].[H-].[Na+]>O1CCCC1.CN(C)C=O.O>[Br:1][C:2]1[S:6]/[C:5](=[N:7]\[C:8]([C:10]23[CH2:11][CH:12]4[CH2:18][CH:16]([CH2:15][CH:14]([CH2:13]4)[CH2:19]2)[CH2:17]3)=[O:9])/[N:4]([CH2:21][CH2:22][O:23][CH3:24])[CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 49760640N-(5-bromo-1,3-thiazol-2-yl)adamantane-1-carboxamide

Product 1

HCID 178495763HCID 178495763, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A solution of Example 131A (2.55 g, 7.43 mmol), 1-bromo-2-methoxyethane (0.77 mL, 8.15 mmol) and sodium hydride (60%) (386 mg, 9.66 mmol) in tetrahydrofuran/N,N-dimethylformamide (2:1) (60 mL) was heated at 75° C. for 12 hours. The mixture was cooled to ambient temperature, diluted with water, and extracted with dichloromethane. The organic extract was dried (Na2SO4), filtered and concentrated. Purification by chromatography (silica gel, 100% dichloromethane) afforded the title compound. MS (ESI) m/z 399 (M+H)+.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (silica gel, 100% dichloromethane)

Sources & evidence

ORD record
ord-7c402f77464f41a7acfbf9fdd31b2503
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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