Dimethylformamide → HCID 67713528, compound

HRID 1378037Notes

Reaction equation

HRID 1378037 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][CH:37]1[CH2:39][CH2:38]1.[CH3:40]N(C)C=O>>[CH:39]1([CH2:38][N:1]([CH2:2][C:3]2[N:7]=[C:6]([C:8]3[N:9]=[CH:10][N:11]4[C:17]5[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=5[C:15](=[O:23])[N:14]5[CH2:24][CH2:25][C@H:13]5[C:12]=34)[O:5][N:4]=2)[CH2:40][CH:32]2[CH2:34][CH2:33]2)[CH2:37][CH2:36]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81503BromomethylcyclopropaneHCID 81531DiisopropylethylamineHCID 53887943HCID 53887943, compound

Product 1

HCID 67713528HCID 67713528, compoundYield 38%

Procedure

4.6 g (12.9 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, 8.6 ml (50.3 mmol) of N-ethyldiisopropylamine and 3.4 ml (32.2 mmol) of bromomethylcyclopropane were stirred at 80° for 18 hours. The reaction solution was evaporated, the residue was dissolved in methylene chloride, the solution was washed three times with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on 110 g of silica gel while eluting with methylene chloride/ethyl acetate 1/1. There were obtained 2.3 g (38%) of (S)-1-[3-(bis-cyclopropylmethylaminomethyl)-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. 155°-160°.

Workup

  1. customThe reaction solution was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washthe solution was washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on 110 g of silica gel
  7. washwhile eluting with methylene chloride/ethyl acetate 1/1

Sources & evidence

ORD record
ord-09fc0db92b78438dad5711c5bbf8e71b
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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