Triethylamine → 7-Chloro-1,2-dimethyl-1H-pyrazolo[3,4-c]pyridin-3(2H)-one
Reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:11](Cl)=[C:10]([C:13]([OH:15])=O)[CH:9]=[CH:8][N:7]=1.Cl.Cl.[CH3:18][NH:19][NH:20][CH3:21].CCN(C(C)C)C(C)C.C(N(CC)CC)C>C(Cl)Cl.O.CN1C(=O)CCC1.CN(C=O)C>[Cl:5][C:6]1[N:7]=[CH:8][CH:9]=[C:10]2[C:13](=[O:15])[N:20]([CH3:21])[N:19]([CH3:18])[C:11]=12Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
Thionyl chloride (92 μl, 1.25 mmol) is added to a mixture of 2,3-dichloro-pyridine-4-carboxylic acid (200 mg, 1.04 mmol), DCM (2 ml) and DMF (20 μl). The mixture is heated to 100° C. for 10 minutes in a microwave. The mixture is concentrated in vacuo. DCM (2.5 ml) and 1,2-dimethylhydrazine dihydrochloride (207 mg, 1.55 mmol) is added before DIPEA (1.35 ml, 7.77 mmol) in DCM (2.5 ml) is added dropwise at RT. Stirring is continued for 1 hour. The mixture is diluted with DCM and extracted with water. The combined organic layers are dried over Na2SO4 and concentrated in vacuo. NMP (1 ml) and triethylamine (200 μl, 1.5 mmol) is added and the mixture heated to 190° C. for 25 minutes in a microwave. At RT water is added (500 μl) and the product purified by RP HPLC. Yield: 50 mg (24%). HPLC-MS: M+H=198; tR=0.44 min (METHOD—1).
Workup
- concentrationThe mixture is concentrated in vacuo
- additionis added dropwise at RT
- extractionextracted with water
- dry with materialThe combined organic layers are dried over Na2SO4
- concentrationconcentrated in vacuo
- temperaturethe mixture heated to 190° C. for 25 minutes in a microwave
- customthe product purified by RP HPLC
Sources & evidence
- ORD record
- ord-f08c84fcb0b64097b7b399ce0e7879d7
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249151B2
Reaction notes
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