Potassium Carbonate → HCID 70075573, compound

HRID 1378041Notes

Reaction equation

HRID 1378041 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]([CH3:12])=[CH:9][CH2:10]Br.[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]4[CH2:34][CH2:35][C@H:25]4[C:24]=23)[N:16]=1>CN(C)C=O>[CH3:7][C:8]([CH3:12])=[CH:9][CH2:10][C:14]([CH2:10][CH:9]=[C:8]([CH3:12])[CH3:7])([NH2:13])[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]4[CH2:34][CH2:35][C@H:25]4[C:24]=23)[N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 53713947HCID 53713947, compound

Product 1

HCID 70075573HCID 70075573, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 g of potassium carbonate and 0.48 ml (4.1 mmol) of dimethylallyl bromide were added to a solution of 660 mg (2 mmol) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-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 dimethylformamide and the mixture was stirred at room temperature for 12 hours. The reaction solution was subsequently filtered and the filtrate was partitioned between methylene chloride and water. The aqueous phase was back-extracted three times with methylene chloride; the combined organic phases were subsequently dried over sodium sulfate, filtered and evaporated. The residue obtained was chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 300:10:1) and there were obtained 650 mg (70%) of (S)-1-[5-[bis-(3-methyl-but-2-enyl)-aminomethyl]-1,2,4-oxadiazol-3-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=0.16 (silica gel, methylene chloride/methanol/aqueous ammonia 300:10:1).

Workup

  1. filtrationThe reaction solution was subsequently filtered
  2. customthe filtrate was partitioned between methylene chloride and water
  3. extractionThe aqueous phase was back-extracted three times with methylene chloride
  4. dry with materialthe combined organic phases were subsequently dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customwas chromatographed (silica gel, methylene chloride/methanol/aqueous ammonia 300:10:1)

Sources & evidence

ORD record
ord-6703a8f2210240488be1d0ae97457dcf
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…