Dibutylamine → HCID 22914244, compound

HRID 1378070Notes

Reaction equation

HRID 1378070 reaction equation
Cl[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:22])=[CH:21][C:16]=4[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=23)[N:4]=1.[CH2:25]([NH:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28]>CN(C)C=O>[CH2:25]([N:29]([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:22])=[CH:21][C:16]=4[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=23)[N:4]=1)[CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 22914351HCID 22914351, compound

Product 1

HCID 22914244HCID 22914244, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.30 g (0.0037 mol) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 15 ml of dimethylformamide was treated with 2.4 g (0.01 9 moll of dibutylamine. After stirring at room temperature for 65 hrs. the orange solution obtained was freed completely from solvent. The residue was chromatographed over silica gel with dichloromethane/methanol 19:1 as the eluent. The product was recrystallized from methanol/ether and there were obtained 1.27 g (77%) of 3-(5-dibutylaminomethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as white crystals; m.p. 137°-140°.

Workup

  1. customthe orange solution obtained
  2. customThe residue was chromatographed over silica gel with dichloromethane/methanol 19:1 as the eluent
  3. customThe product was recrystallized from methanol/ether

Sources & evidence

ORD record
ord-66243f436a04412193bce8298492c70c
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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