Hydrochloric Acid → (S)-6-(3-Amino-pyrrolidin-1-yl)-5-cyano-2-hydroxy-benzo[de] isoquinoline-1,3-dione, Hydrochloride

HRID 567032Notes

Reaction equation

HRID 567032 reaction equation
[C:1]([C:3]1[C:4]([N:19]2[CH2:23][CH2:22][C@H:21]([NH:24]C(=O)OC(C)(C)C)[CH2:20]2)=[C:5]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:6]2=[C:7]([CH:18]=1)[C:8](=[O:17])[N:9]([OH:16])[C:10]3=[O:15])#[N:2].[ClH:32]>CCO>[ClH:32].[NH2:24][C@H:21]1[CH2:22][CH2:23][N:19]([C:4]2[C:3]([C:1]#[N:2])=[CH:18][C:7]3[C:8](=[O:17])[N:9]([OH:16])[C:10](=[O:15])[C:11]4[C:6]=3[C:5]=2[CH:14]=[CH:13][CH:12]=4)[CH2:20]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86756249(S)-[1-(5-cyano-2-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester

Product 1

HCID 131722282(S)-6-(3-Amino-pyrrolidin-1-yl)-5-cyano-2-hydroxy-benzo[de] isoquinoline-1,3-dione, Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The (S)-[1-(5-cyano-2-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester from above was dissolved in EtOH and reacted with a stream of HCl gas forming a precipitate which was collected by filtration and dried to give 0.021 g of the title compound, mp>250° C.

Workup

  1. customforming a precipitate which
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-aeed081bde094e11a2d1f16798343477
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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