Dichloromethane → HCID 70092318, compound

HRID 1378043Notes

Reaction equation

HRID 1378043 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][CH2:37][C@H:26]4[C:25]=23)[O:18][N:17]=1.[CH2:38](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][CH2:37][C@H:26]4[C:25]=23)[O:18][NH:17][CH:16]=[N:20]1)[CH2:7][CH:9]=[CH2:38])[CH:11]=[CH2:12]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 54219737HCID 54219737, compound

Product 1

HCID 70092318HCID 70092318, compoundYield 82%

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 685 mg (2 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]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 over magnesium sulfate, filtered and evaporated. The residue obtained was chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 200:10:1). There were obtained 693 mg (82%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-5-yl)-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-8-one as a colourless foam, Rf=0.32 (silica gel, methylene chloride/methanol/aqueous ammonia 200:10:1).

Workup

  1. washwashed three times with water
  2. dry with materialThe organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customwas chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 200:10:1)

Sources & evidence

ORD record
ord-2143986a583248eaa2990706ac2c887a
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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