Hydrochloric Acid → Hydrochloric Acid

HRID 1661114Notes

Reaction equation

HRID 1661114 reaction equation
C(OC([NH:8][C@@H:9]([CH:50]([CH3:52])[CH3:51])[C:10]([O:12][C@H:13]([C:15]1[N:19]2[N:20]([CH2:38][C:39]3[C:40]([CH3:49])=[N:41][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:43][CH:44]=3)[C:21](=[O:37])[C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:23]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:18]2=[N:17][N:16]=1)[CH3:14])=[O:11])=O)(C)(C)C.[ClH:53]>>[NH2:8][C@@H:9]([CH:50]([CH3:52])[CH3:51])[C:10]([O:12][C@H:13]([C:15]1[N:19]2[N:20]([CH2:38][C:39]3[C:40]([CH3:49])=[N:41][C:42]([C:45]([F:46])([F:48])[F:47])=[CH:43][CH:44]=3)[C:21](=[O:37])[C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:23]([C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)[C:18]2=[N:17][N:16]=1)[CH3:14])=[O:11].[ClH:53]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59177922HCID 59177922, compound

Product 2

HCID 313Hydrochloric AcidYield 85%HCID 59177910HCID 59177910, compound

Procedure

To a round bottom flask was added (S)—((S)-1-(8-(4-chlorophenyl)-5-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-7-phenyl-5,6-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethyl) 2-( tert-butoxycarbonylamino)-3-methylbutanoate (39 mg, 0.529 mmol) and 4N HCl (2 ml). The reaction was stirred at rt for 30 min. After this time, the solution was concentrated under reduced pressure. To the residue was added CH2Cl2(2 ml) and hexanes (2 ml). The solvent was decanted. The remaining solid was dried under vacuum to give product (S)—((S)-1-(8-(4-chlorophenyl)-5-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-7-phenyl-5,6-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethyl) 2-amino-3-methylbutanoate as an HCl salt (30mg, 85% yield).

Workup

  1. concentrationAfter this time, the solution was concentrated under reduced pressure
  2. additionTo the residue was added CH2Cl2(2 ml) and hexanes (2 ml)
  3. customThe solvent was decanted
  4. customThe remaining solid was dried under vacuum

Sources & evidence

ORD record
ord-21e52006d5f640c891689ffce7100dfa
Source dataset
uspto-grants-2011_10
Patent number
US08030306B2

Reaction notes

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