Hydrochloric Acid → (S)-8-chloro-1-(4-dipropylaminomethyl-thiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one hydrochloride

HRID 1737362Notes

Reaction equation

HRID 1737362 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:31])[N:9]3[CH2:30][CH2:29][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[S:17][CH:18]=[C:19]([CH2:21][N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl>ClCCl>[ClH:1].[Cl:1][C:2]1[C:7]2[C:8](=[O:31])[N:9]3[CH2:30][CH2:29][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[S:17][CH:18]=[C:19]([CH2:21][N:22]([CH2:23][CH2:24][CH3:25])[CH2:26][CH2:27][CH3:28])[N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86753959(S)-8-chloro-1-(4-dipropylaminomethyl-thiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-one

Product 1

HCID 86753960(S)-8-chloro-1-(4-dipropylaminomethyl-thiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one hydrochlorideYield 172.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.91 g (0.0020 mol) of (S)-8-chloro-1-(4-dipropylaminomethyl-thiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one in 30 ml of dichloromethane was treated with 0.54 ml (0.0020 mol) of 3.7N ethanolic hydrochloric acid. After stirring at room temperature for 10 minutes the solution was completely freed from the solvents. The residue was recrystallized from ethanol/ether. There was obtained 0.85 g (87%) of (S)-8-chloro-1-(4-dipropylaminomethyl-thiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one hydrochloride (1:1) as white crystals; m.p. 221-223° and [α]D20 =-245.7° (MeOH, c=1%).

Workup

  1. customThe residue was recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-6dd2354d99ca4e2eaac2d89c1223e484
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

Loading…