Sodium hydride → HCID 23498628, compound

HRID 1836205Notes

Reaction equation

HRID 1836205 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]2[S:17][C:18]3[CH2:23][N:22]([C:24]([O-:26])=[O:25])[CH2:21][CH2:20][C:19]=3[C:6]=2[CH2:5][NH:4][CH2:3]1.[H-].[Na+].Br[CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33].[Cl-:35].[NH4+]>C(OCC)(=O)C>[Cl:35][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:5]1[N:4]([CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])[CH2:3][C:2](=[O:1])[N:8]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]2[S:17][C:18]3[CH2:23][N:22]([C:24]([O:26][C:6]([CH3:19])([CH3:7])[CH3:5])=[O:25])[CH2:21][CH2:20][C:19]=3[C:6]1=2

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 700922-Butene, 1-bromo-3-methyl-HCID 86759504HCID 86759504, compound

Product 1

HCID 23498628HCID 23498628, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

0.5 g of t-butyl 5-2-chlorophenyl)-1,2,3,4,5,6,7,9-octahydro-2-oxo-1-(2-phenylethyl)-8H-pyrido[4′,3′:4,5]thieno[2,3-e]-1,4-diazepine-8-carboxylate (1 mmol) is dissolved in anhydrous tetrahydrofuiran (20 ml). Sodium hydride dispersed at 60% (0.028 g, 1.1 mmol) is added by portions. The reaction meum is left until release ends then 1-bromo-3-methyl-2-butene (0.125 ml, 1.1 Immol) is added dropwise. Agitation is carried out for 3 hours at 23° C. and the reaction medium is heated all night at 60° C. then the halogenated derivative (0.125 ml, 1.1 mmol) is added. After heating for 48 hours at 60° C., the reaction medium is poured into a saturated solution of ammonium chloride (30 ml) then ethyl acetate (30 ml) is added. After decanting, the aqueous phase is extracted with ethyl acetate (30ml). The organic phase is dried over magnesium sulphate, filtered and the solvent-is evaporated off. After purification by chromatography on a silica column (eluent: ethyl acetate-heptane: 20-80 to 50-50), the fractions containing only the product are evaporated and the desired product is obtained in the form of a pale yellow amorphous powder (0.47 g, 79%).

Workup

  1. additionis added by portions
  2. waitThe reaction meum is left until release
  3. additionthe halogenated derivative (0.125 ml, 1.1 mmol) is added
  4. temperatureAfter heating for 48 hours at 60° C.
  5. customAfter decanting
  6. extractionthe aqueous phase is extracted with ethyl acetate (30ml)
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent-is evaporated off
  10. customAfter purification by chromatography on a silica column (eluent: ethyl acetate-heptane: 20-80 to 50-50)
  11. additionthe fractions containing only the product
  12. customare evaporated

Sources & evidence

ORD record
ord-146e96344f6d4cfcbfde0de13d09c4c4
Source dataset
uspto-grants-2004_08
Patent number
US06777408B1

Reaction notes

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