1-Bromopropane → HCID 22914618, compound

HRID 1378106Notes

Reaction equation

HRID 1378106 reaction equation
C(N(C(C)C)[CH:4]([CH3:6])[CH3:5])C.Br[CH2:11][CH2:12][CH3:13].[NH2:14][CH2:15][C:16]1[O:20][N:19]=[C:18]([C:21]2[N:22]=[CH:23][N:24]3[C:30]4[CH:31]=[CH:32][S:33][C:29]=4[C:28](=[O:34])[N:27]([CH3:35])[CH2:26][C:25]=23)[N:17]=1>CN(C)C=O>[CH2:11]([N:14]([CH2:15][C:16]1[O:20][N:19]=[C:18]([C:21]2[N:22]=[CH:23][N:24]3[C:30]4[CH:31]=[CH:32][S:33][C:29]=4[C:28](=[O:34])[N:27]([CH3:35])[CH2:26][C:25]=23)[N:17]=1)[CH2:5][CH2:4][CH3:6])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 81531DiisopropylethylamineHCID 22914212HCID 22914212, compound

Product 1

HCID 22914618HCID 22914618, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7 ml (23 mmol)of N-ethyldiisopropylamine and 0.9 ml (9.9 mmol) of 1-bromopropane were added to a solution of 1.5 g (4.74 mmol) of 3-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-6-one in 40 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 250:10:1). There were obtained 930 mg (49%) of 3-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-6-one of m.p. 128.5°-130.0°.

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 250:10:1)

Sources & evidence

ORD record
ord-4b65551e48714db4b5be06ed54afbfd5
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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