Dimethylformamide → HCID 22876582, compound

HRID 1378036Notes

Reaction equation

HRID 1378036 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][C@H:13]4[C:12]=23)[O:5][N:4]=1.C(N([CH:32]([CH3:34])[CH3:33])C(C)C)C.Br[CH2:36][CH2:37][CH:38]=[CH2:39].[CH3:40]N(C)C=O>>[CH2:36]([N:1]([CH2:2][C:3]1[N:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][C@H:13]4[C:12]=23)[O:5][N:4]=1)[CH2:40][CH2:34][CH:32]=[CH2:33])[CH2:37][CH:38]=[CH2:39]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 21241Homoallyl bromideHCID 81531DiisopropylethylamineHCID 53887943HCID 53887943, compound

Product 1

HCID 22876582HCID 22876582, compoundYield 53%

Procedure

4 g (11.2 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-one, 25 ml of N,N-dimethylformamide, 7.5 ml (43.7 mmol) of N-ethyldiisopropylamine and 2.9 ml (28 mmol) of 4-bromo-1-butene were stirred at 800 for 25 hours. The reaction solution was evaporated, the residue was dissolved in methylene chloride, this solution was washed three times with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on 160 g of silica gel while eluting with methylene chloride/ethyl acetate 1/1. There were obtained 2.8 g (53%) of (S)-1-{3-[bis-(but-3-enyl)aminomethyl]-1,2,4-oxadiazol-5-yl}-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the hydrochloride of m.p. 115°-120°.

Workup

  1. customThe reaction solution was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washthis solution was washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on 160 g of silica gel
  7. washwhile eluting with methylene chloride/ethyl acetate 1/1

Sources & evidence

ORD record
ord-e5f8a6aa0d584e9fac0a6bffe3d373bf
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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