Dichloromethane → HCID 70094026, compound

HRID 1378102Notes

Reaction equation

HRID 1378102 reaction equation
C([N:3]([CH:7]([CH3:9])C)[CH:4](C)C)C.[CH2:10](Br)[CH:11]=[CH2:12].NC[C:16]1[N:20]=[C:19]([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]4[CH2:35][CH2:36][C@H:26]4[C:25]=23)[O:18][N:17]=1.[CH2:37](Cl)Cl>>[CH2:10]([N:3]([CH2:4][C:19]1([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]4[CH2:35][CH2:36][C@H:26]4[C:25]=23)[O:18][NH:17][CH:16]=[N:20]1)[CH2:7][CH:9]=[CH2:37])[CH:11]=[CH2:12]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 53986672HCID 53986672, compound

Product 1

HCID 70094026HCID 70094026, compoundYield 79%

Procedure

2.4 ml (13.8 mmol) of N-ethyldiisopropylamine and 0.67 ml (8 mmol) of allyl bromide were added to a solution of 756 mg (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 methylenechloride 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 residue obtained was chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:1). There were obtained 645 mg (79%) of (S)-1-(5-diallylaminomethyl-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=0.52 (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:1).

Workup

  1. washwashed three times with water
  2. dry with materialThe organic phases were dried with magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customwas chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:1)

Sources & evidence

ORD record
ord-70308167edba405cb0e9dc15c626b5d1
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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