Potassium Carbonate → HCID 69673195, compound
Reaction equation
[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:12]=2[C:13]([NH:15][CH:16]([CH2:21][OH:22])C(OC)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:29](N(S(F)(F)F)CC)C.[C:38](=[O:41])([O-])[O-:39].[K+].[K+]>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:12]=2[C:13]2[O:22][CH2:21][CH:16]([C:38]([O:39][CH3:29])=[O:41])[N:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -76 °C
Procedure
To a solution of methyl 2-(3,5-diphenylpyridazine-4-carboxamido)-3-hydroxypropanoate (220 mg, 0.58 mmol) in DCM (15 mL), (diethylamino)sulfur trifluoride (188 mg, 1.16 mmol) was added at −76° C. and stirred at −76° C. for 2 h. Potassium carbonate (400 mg, 2.8 mmol) was added to the reaction mixture at −78° C. and the resulting reaction mixture was warmed to rt. Reaction was quenched by addition of saturated Na2CO3, extracted with DCM (2×25 mL), washed with brine (1×10 mL) and dried over anhy. Na2SO4. Evaporation of the solvent under reduced pressure gave crude product methyl 2-(3,5-diphenylpyridazin-4-yl)-4,5-dihydrooxazole-4-carboxylate (compound 25) (130 mg, 61%) as an off white solid.
Workup
- customthe resulting reaction mixture
- temperaturewas warmed to rt
- customReaction
- customwas quenched by addition of saturated Na2CO3
- extractionextracted with DCM (2×25 mL)
- washwashed with brine (1×10 mL)
- customdried over anhy
- customEvaporation of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-974e9794e18244e5924f383c0ef59e2d
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145372B2
Reaction notes
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