Allyl bromide → HCID 22876572, compound

HRID 1377994Notes

Reaction equation

HRID 1377994 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][C:20]([F:23])=[C:21]([Cl:22])[C:16]=4[C:15](=[O:24])[N:14]4[CH2:25][CH2:26][C@H:13]4[C:12]=23)[N:4]=1.C(N(C(C)C)[CH:30]([CH3:32])[CH3:31])C.[CH2:36](Br)[CH:37]=[CH2:38]>C(Cl)Cl>[CH2:32]([N:1]([CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][C:20]([F:23])=[C:21]([Cl:22])[C:16]=4[C:15](=[O:24])[N:14]4[CH2:25][CH2:26][C@H:13]4[C:12]=23)[N:4]=1)[CH2:38][CH:37]=[CH2:36])[CH:30]=[CH2:31]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 53982526(S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

Product 1

HCID 22876572HCID 22876572, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

26.6 g (71 mmol) of crude (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 400 ml of methylene chloride, 85 ml (496 mmol) of N-ethyldiisopropylamine and 34.5 g (285 mmol) of allyl bromide were stirred at room temperature for 20 hours. The reaction solution was washed three times with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on 2 kg of silica gel while eluting with ethyl acetate. The uniform fractions were evaporated and recrystallized from toluene and n-hexane. There were obtained 22.34 g (69%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 103°-104°.

Workup

  1. washThe reaction solution was washed three times with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was chromatographed on 2 kg of silica gel
  5. washwhile eluting with ethyl acetate
  6. customThe uniform fractions were evaporated
  7. customrecrystallized from toluene and n-hexane

Sources & evidence

ORD record
ord-8824c2d369124cbaa29d2dcc0d296f3a
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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