Hydrochloric Acid → HCID 86753945, compound

HRID 1418905Notes

Reaction equation

HRID 1418905 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:32])[N:9]3[CH2:31][CH2:30][CH2:29][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:22]([CH2:26][CH:27]=[CH2:28])[CH2:23][CH:24]=[CH2:25])=[CH:19][N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[C:7]2[C:8](=[O:32])[N:9]3[CH2:31][CH2:30][CH2:29][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:22]([CH2:23][CH:24]=[CH2:25])[CH2:26][CH:27]=[CH2:28])=[CH:19][N:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86753944HCID 86753944, compound

Product 1

HCID 86753945HCID 86753945, compoundYield 145.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.15 g (0.00255 mol) of (S)-8-chloro-1-(5-diallylaminomethyl-oxazol-2-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one in 20 ml of ethanol were treated with 0.53 ml (0.00253 mol) of 4.78N ethanolic hydrochloric acid at 0°. After stirring at 0° for 10 minutes the colorless solution was completely freed from the solvents. The residue was dissolved in hot ethanol and recrystallized by the addition of ether. There was obtained 0.9 g (78%) of (S)-8-chloro-1-(5-diallylaminomethyl-oxazol-2-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one hydrochloride (1:1) as beige crystals; m.p. 169°-171° and [α]D20 =+7.70 (MeOH, c=1%).

Workup

  1. customrecrystallized by the addition of ether

Sources & evidence

ORD record
ord-f0e1542eeea64199b4ec36072cc54db3
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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