Methanol → 9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine

HRID 1739890Notes

Reaction equation

HRID 1739890 reaction equation
O=[C:2]1[NH:8][C:7]2[S:9][CH:10]=[CH:11][C:6]=2[CH2:5][N:4]2[CH:12]=[CH:13][CH:14]=[C:3]12.[B].CSC.CO>O1CCCC1>[S:9]1[C:7]2[NH:8][CH2:2][C:3]3[N:4]([CH:12]=[CH:13][CH:14]=3)[CH2:5][C:6]=2[CH:11]=[CH:10]1

Participants

5

Reactant 3

HCID 887MethanolHCID 9833925Boron, trihydro(thiobis(methane))-, (T-4)-HCID 110418649-oxo-9,10-dihydro-4H-pyrrolo[1,2-a]-thieno[2,3-e][1,4]diazepine

Product 1

HCID 218371599,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 7.0 g of 9-oxo-9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepin in 25 ml of anhydrous tetrahydrofuran is added 9 ml of 10 molar boron-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours. The solution is cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum. To the residue is added 100 ml of 2 N NaOH. The mixture is refluxed 5 hours and filtered. The solid is extracted with dichloromethane and the extract is washed with 2 N citric acid, water and dried (Na2SO4). The solvent is removed in vacuo to give the desired product as a solid.

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. customThe volatiles are removed under vacuum
  3. additionTo the residue is added 100 ml of 2 N NaOH
  4. temperatureThe mixture is refluxed 5 hours
  5. filtrationfiltered
  6. extractionThe solid is extracted with dichloromethane
  7. washthe extract is washed with 2 N citric acid, water
  8. dry with materialdried (Na2SO4)
  9. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2cb388f860474a4cab9cbbe5df84d43a
Source dataset
uspto-grants-1999_10
Patent number
US05968937

Reaction notes

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