Ethyl Bromide → HCID 22914417, compound

HRID 1378110Notes

Reaction equation

HRID 1378110 reaction equation
[CH2:1]([N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])C)[CH3:2].Br[CH2:11][CH3:12].NCC1[O:19][N:18]=[C:17]([C:20]2[N:21]=[CH:22][N:23]3[C:29]4[S:30][CH:31]=CC=4[C:27](=[O:33])[N:26]([CH3:34])[CH2:25][C:24]=23)[N:16]=1>CN(C)C=O>[CH2:7]([N:3]([CH2:1][C:2]1[O:19][N:18]=[C:17]([C:20]2[N:21]=[CH:22][N:23]3[C:29]4[S:30][CH:31]=[CH:11][C:12]=4[C:27](=[O:33])[N:26]([CH3:34])[CH2:25][C:24]=23)[N:16]=1)[CH2:4][CH3:6])[CH3:9]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 81531DiisopropylethylamineHCID 22914458HCID 22914458, compound

Product 1

HCID 22914417HCID 22914417, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.75 ml (21.8 mmol) of N-ethyldiisopropylamine and 0.94 ml (12.6 mmol) of 1-bromoethane were added to a solution of 1.0 g (3.16 mmol) of 7-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepin-4-one in 30 ml of dimethylformamide and the mixture was stirred at 70° for 1 hour. The reaction solution was subsequently evaporated, whereupon the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous phase was washed three times with methylene chloride. The organic phases were dried with magnesium sulfate, filtered and evaporated. The residue obtained was chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 110:10:1). There were obtained 250 mg (21%) of 7-(5-diethylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepin-4-one as a colourless foam, Rf=0.56 (silica gel, methylene chloride/methanol/aqueous ammonia 110:10:1).

Workup

  1. customThe reaction solution was subsequently evaporated, whereupon the residue
  2. customwas partitioned between methylene chloride and 2N sodium carbonate solution
  3. washThe aqueous phase was washed three times with methylene chloride
  4. dry with materialThe organic phases were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customwas chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 110:10:1)

Sources & evidence

ORD record
ord-9cdf73a18cbb443ea5b00e79dc7ce72c
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…