Ethyl Bromide → HCID 22914483, compound

HRID 1378112Notes

Reaction equation

HRID 1378112 reaction equation
[CH2:1](N(C(C)C)C(C)C)[CH3:2].[CH2:10](Br)[CH3:11].[NH2:13][CH2:14][C:15]1[O:19][N:18]=[C:17]([C:20]2[N:21]=[CH:22][N:23]3[C:29]4[CH:30]=[CH:31][S:32][C:28]=4[C:27](=[O:33])[N:26]([CH3:34])[CH2:25][C:24]=23)[N:16]=1>CN(C)C=O>[CH2:1]([N:13]([CH2:14][C:15]1[O:19][N:18]=[C:17]([C:20]2[N:21]=[CH:22][N:23]3[C:29]4[CH:30]=[CH:31][S:32][C:28]=4[C:27](=[O:33])[N:26]([CH3:34])[CH2:25][C:24]=23)[N:16]=1)[CH2:10][CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 81531DiisopropylethylamineHCID 22914212HCID 22914212, compound

Product 1

HCID 22914483HCID 22914483, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.35 ml (13.6 mmol) of N-ethyldiisopropylamine and 0.76 ml (10.2 mmol) of ethyl bromide were added to a solution of 0.54 g (1.7 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 20 ml 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 over magnesium sulfate, filtered and evaporated. The residue obtained was chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 110:10:1). There were obtained 301 mg (47%) of 3-(5-diethylaminomethyl-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 as a colourless foam, Rf=0.66 (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 over 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-a69d982ab6da4df88da610cd35cd02ac
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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