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 1418946Notes

Reaction equation

HRID 1418946 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-a8350001d1a445dfbc73654a198f1df4
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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