Triethylamine → HCID 50903082, compound
Reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.[N:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][N:11]=1.[CH2:17](N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C)C=O.[Cl-].[Na+].O>[CH3:17][N:16]([C:13]1[CH:14]=[CH:15][N:10]=[N:11][CH:12]=1)[C:7]([C:5]1[N:6]=[C:2]([Cl:1])[S:3][CH:4]=1)=[O:9]Participants
Procedure
200 mg (1.2 mmol) of 2-chlorothiazole-4-carboxylic acid and 96.1 mg (0.9 mmol) of pyridazin-4-yl-amine were dissolved in 6 ml dimethyl formamide. 0.15 mL (1.1 mmol) of triethyl amine followed by 382 mg (0.73 mmol) of 1H-Benzotriazol-1-yloxytri-pyrrolidinophosphonium hexafluorophosphate (PyBOP) were added and the reaction mixture was stirred at room temperature for 16 h. Brine was added and the reaction mixture was extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The obtained residue was purified by flash column chromatography (silica, gradient elution cyclohexane, ethyl acetate, methanol) to give 200 mg (61%, 95% purity) of the title compound.
Workup
- additionwere added
- extractionthe reaction mixture was extracted three times with dichloromethane
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customThe obtained residue was purified by flash column chromatography (silica, gradient elution cyclohexane, ethyl acetate, methanol)
Sources & evidence
- ORD record
- ord-afcbf4a1510d45e0a61c94bd573f7b49
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029639B2
Reaction notes
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