Reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([O-:9])=O)=[N:4][N:3]=1.[K+].C(Cl)(=O)C(Cl)=O.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[C:27](=[CH:28][C:29]([O:33][C@H:34]([C:38]4[CH:43]=[CH:42][CH:41]=[C:40]([O:44][CH3:45])[CH:39]=4)[C@@H:35]([NH2:37])[CH3:36])=[CH:30][CH:31]=3)[CH:26]=[N:25]2)=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C.N>C1COCC1.CCOC(C)=O.C(#N)C>[F:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:32]3[C:27](=[CH:28][C:29]([O:33][C@H:34]([C:38]4[CH:43]=[CH:42][CH:41]=[C:40]([O:44][CH3:45])[CH:39]=4)[C@@H:35]([NH:37][C:7]([C:5]4[O:6][C:2]([CH3:1])=[N:3][N:4]=4)=[O:9])[CH3:36])=[CH:30][CH:31]=3)[CH:26]=[N:25]2)=[CH:22][CH:23]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 2.5 °C
Procedure
Potassium 5-methyl-[1,3,4]oxadiazole-2-carboxylate (31.8 mg, 0.19 mmol) was mixed with acetonitrile (195 μl). A slurry was formed. The mixture was cooled to 0-5° C. oxalyl chloride (14.99 μl, 0.17 mmol) was added and the reaction was stirred for 1 h at 0-5° C. (1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-1-(3-methoxyphenyl)propan-2-amine (6a, 25 mg, 0.06 mmol) was dissolved in dry THF (400 μl). N,N-diisopropylethylamine (65.6 μl, 0.38 mmol) was added. The THF solution was cooled to 0-5° C. The acid chloride slurry was drop wise added to the amine solution. The reaction was stirred at 0-5° C. After 1.5 h the reaction was poured into a mixture of EtOAc and diluted ammonia (ca 5%). The mixture was shaken, the organic layer collected. The water phase was washed twice with EtOAc. The combined organic layers were dried over sodium sulphate.
Workup
- customA slurry was formed
- additionwas added
- stirringThe mixture was shaken
- customthe organic layer collected
- washThe water phase was washed twice with EtOAc
- dry with materialThe combined organic layers were dried over sodium sulphate
Sources & evidence
- ORD record
- ord-8a6a23443f27494f986d7eb5074c2998
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728030B2
Linked notes
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