2-Butene, 1-bromo-3-methyl- → HCID 131720188, compound
Reaction equation
C(N(C(C)C)C(C)C)C.CC(C)=CCBr.NCC1N=C([C:23]2[N:24]=[CH:25][N:26]3[C:32]4[CH:33]=[CH:34][S:35][C:31]=4[C:30](=[O:36])[N:29]4[CH2:37][CH2:38][C@H:28]4[C:27]=23)ON=1>C(Cl)Cl>[CH:23]1[N:24]=[CH:25][N:26]2[C:32]3[CH:33]=[CH:34][S:35][C:31]=3[C:30](=[O:36])[N:29]3[CH2:37][CH2:38][CH:28]3[C:27]=12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1.5 ml (8.6 mmol) of N-ethyldiisopropylamine and 0.28 ml (2.4 mmol) of dimethylallyl bromide were added to a solution of 453 mg (1.2 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-11,11a-dihydro-8H, 10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one in 20 ml of methylene chloride and the mixture was stirred at room temperature for 20 hours. The reaction solution was subsequently diluted with methylene chloride and washed three times with water. The organic phases were dried with magnesium sulfate, filtered and evaporated. The is residue obtained was chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:1). There were obtained 240 mg (43%) of (S)-1-[3-bis-[3-methyl-but-2-enyl)-aminomethyl]-1,2,4-oxadiazol-5-yl]-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one as a colourless foam, Rf=0.55 (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:1).
Workup
- washwashed three times with water
- dry with materialThe organic phases were dried with magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe is residue obtained
- customwas chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:1)
Sources & evidence
- ORD record
- ord-c907df6075d946e49c82ae3561809fe4
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665718
Reaction notes
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