Hydrochloric Acid → HCID 86711929, compound
Reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[C:10](N)[CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)[N:16]=2)[N:3]=1.N([O-])=O.[Na+].[S:35](=[O:37])=[O:36].[ClH:38]>C(O)(=O)C.O>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[C:10]([S:35]([Cl:38])(=[O:37])=[O:36])[CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)[N:16]=2)[N:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)benzenamine (Example 78, 100 mg, 0.24 mmol) in acetic acid (4 mL) and hydrochloric acid (37% aq., 0.5 mL) at 0° C., was added a solution of sodium nitrite (33 mg, 0.48 mmol) in H2O (1 mL) and the resulting mixture was stirred for 1 h at 0° C. Sulfur dioxide (0.9 M solution in AcOH 4 mL) and CuCl2 (20 mg, 0.20 mmol) were then added at 0° C., and the resulting mixture was stirred at RT for 16 h. The mixture was poured onto H2O (50 mL) and extracted with EtOAc (50 mL). The organic phase was washed with aq. sodium bicarbonate and brine, dried (Na2SO4), filtered and concentrated under reduced pressure to afford the title compound as a yellow solid (72 mg, 69.3%). LC-MS (ES+) C19H13ClF3N5O4S requires: 499. found: 500 (M+H)+.
Workup
- stirringthe resulting mixture was stirred at RT for 16 h
- additionThe mixture was poured onto H2O (50 mL)
- extractionextracted with EtOAc (50 mL)
- washThe organic phase was washed with aq. sodium bicarbonate and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8239bba1fa554f7d9d8ce31ba0441df0
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018380B2
Reaction notes
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