Dimethylformamide → HCID 22876581, compound

HRID 1378128Notes

Reaction equation

HRID 1378128 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]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]4[CH2:23][CH2:24][C@H:13]4[C:12]=23)[O:5][N:4]=1.C(N([CH:31]([CH3:33])[CH3:32])C(C)C)C.Br[CH2:35][CH2:36][CH:37]=[CH2:38].[CH3:39]N(C)C=O>>[CH2:35]([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]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]4[CH2:23][CH2:24][C@H:13]4[C:12]=23)[O:5][N:4]=1)[CH2:39][CH2:33][CH:31]=[CH2:32])[CH2:36][CH:37]=[CH2:38]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 21241Homoallyl bromideHCID 81531DiisopropylethylamineHCID 54124626HCID 54124626, compound

Product 1

HCID 22876581HCID 22876581, compoundYield 15%

Procedure

2.98 g (9.25 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-12,12a-dihydro-9H,11H-azeto[2, 1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one were stirred at 75° for 60 hours with 3.2 g (25 mmol) of N-ethyldiisopropylamine and 2.5 g (18.5 mmol) of 4-bromo-1-butene in 20 ml of N,N-dimethylformamide. By evaporation of the solvent and chromatography of the residue on silica gel while eluting with ethyl acetate there was obtained 0.62 g (15%) of (S)-1-{3-[bis-(but-3-enyl)aminomethyl]-1,2,4-oxadiazol-5-yl}-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. 80°-87°.

Workup

  1. customBy evaporation of the solvent and chromatography of the residue on silica gel
  2. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-f9307e3ca74e4868956b68d6ad6dd5a2
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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