HCID 67502877, compound → HCID 57691318, compound

HRID 1513745Notes

Reaction equation

HRID 1513745 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH2:17][O:18][C:19]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=5)[N:22]=[CH:21][CH:20]=4)=[N:15][N:16]=3)[N:13]=2)[CH:5]=[CH:4][C:3]=1[C@@H:31]([NH:36][S@](C(C)(C)C)=O)[C:32]([F:35])([F:34])[F:33]>CO.Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH2:17][O:18][C:19]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=5)[N:22]=[CH:21][CH:20]=4)=[N:15][N:16]=3)[N:13]=2)[CH:5]=[CH:4][C:3]=1[C@@H:31]([NH2:36])[C:32]([F:33])([F:35])[F:34]

Participants

4

Reactant 1

HCID 67502877HCID 67502877, compound

Product 1

HCID 57691318HCID 57691318, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of (S)-N-((R)-1-(2-chloro-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide (62 mg, 100 μmol) in MeOH (2 mL) and 5M HCl (2 mL) was stirred at 35° C. for 18 h. LCMS suggests full conversion. Solvents removed under reduced pressure and residue dissolved in MeOH (20 mL). Si-Carbonate (1.3 g; 0.9 mmol) added to solution and stirred for 2 h. Filtrated isolated by filtration and reduced to a film under reduced pressure. Product purified on silica (4 g) eluting with 7% 2M NH3 in MeOH/DCM. MS (ESI pos. ion) m/z: 515 (MH+). Calc'd exact mass for C24H18ClF3N6O2: 514.

Workup

  1. customSolvents removed under reduced pressure and residue
  2. dissolutiondissolved in MeOH (20 mL)
  3. filtrationFiltrated
  4. customisolated by filtration
  5. customProduct purified on silica (4 g)
  6. washeluting with 7% 2M NH3 in MeOH/DCM

Sources & evidence

ORD record
ord-ab583170c02a464f9f9e32db4a7fff20
Source dataset
uspto-grants-2012_07
Patent number
US08217177B2

Reaction notes

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