HCID 67502877, compound → HCID 57691318, compound

HRID 40286Notes

Reaction equation

HRID 40286 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-1fbfd4e2ecf14beaa6c51205d35e387b
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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