Dipropylamine → HCID 54508587, compound

HRID 1378085Notes

Reaction equation

HRID 1378085 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][C:18]([CH2:21]Cl)=[N:19][N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:27]([NH:30][CH2:31][CH2:32][CH3:33])[CH2:28][CH3:29]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][C:18]([CH2:21][N:30]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:28][CH3:29])=[N:19][N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 54273189HCID 54273189, compound

Product 1

HCID 54508587HCID 54508587, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.30 g (3.33 mmol) of (S)-8-chloro-1-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one in 10 ml of N,N-dimethylformamide was treated with 1.7 g (0.017 mol) of dipropylamine. After stirring at room temperature for 20 hrs. and at 80° C. for 4 hrs. the solution obtained was completely freed from the solvents. The residue was chromatographed over silica gel with methylene chloride/methanol 39:1 as the eluent. The product was recrystallized from ether. There were obtained 1.27 g (85%) of (S)-8-chloro-1-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1- c][1,4]benzodiazepin-9-one as white crystals; m.p. 158°-160° and [a]D20 =48.8° (CH2Cl2, c=1%).

Workup

  1. waitand at 80° C. for 4 hrs
  2. customthe solution obtained
  3. customThe residue was chromatographed over silica gel with methylene chloride/methanol 39:1 as the eluent
  4. customThe product was recrystallized from ether

Sources & evidence

ORD record
ord-00cd0bb589364690887e114ee85fc2c1
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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