Pyrrolidine → HCID 22914635, compound

HRID 1378072Notes

Reaction equation

HRID 1378072 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.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>CN(C)C=O>[F:22][C:20]1[CH:19]=[CH:18][C:17]2[N:11]3[CH:10]=[N:9][C:8]([C:5]4[N:4]=[C:3]([CH2:2][N:25]5[CH2:29][CH2:28][CH2:27][CH2:26]5)[O:7][N:6]=4)=[C:12]3[CH2:13][N:14]([CH3:24])[C:15](=[O:23])[C:16]=2[CH:21]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 22914351HCID 22914351, compound

Product 1

HCID 22914635HCID 22914635, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.50 g (0.0043 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 1.5 g (0.022 mol) of pyrrolidine. After stirring at room temperature for 65 hrs. the yellow-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. There were obtained 1.35 g (82%) of 8-fluoro-5-methyl-3-(5-pyrrolidin-1-ylmethyl-1,2,4-oxadiazol-3-yl)-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as white crystals; m.p. 158°-160°.

Workup

  1. customthe yellow-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-b93c299ab1db4c338dddeec13103a023
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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