Pyrazole → (4-Chloro-phenyl)-(6-pyrazol-1-yl-pyrazin-2-yl)-amine
Reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.C(OC(=O)[N:14]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[N:19][CH:18]=[C:17](Cl)[N:16]=1)(C)(C)C.C(OCC)(=O)C.CCCCCCC>CN(C)C=O>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([NH:14][C:15]2[CH:20]=[N:19][CH:18]=[C:17]([N:3]3[CH:7]=[CH:6][CH:5]=[N:4]3)[N:16]=2)=[CH:27][CH:26]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Sodium hydride (60% in mineral oil, 156 mg, 3.90 mmol) was added to a suspension of pyrazole (260 mg, 3.82 mmol) in N,N-dimethylformamide (5 mL) and the mixture was heated to 50° C. for 20 minutes. (4-Chloro-phenyl)-(6-chloro-pyrazin-2-yl)-carbamic acid tert-butyl ester (260 mg, 0.76 mmol) was added and stirring was continued for 30 minutes at the same temperature. The temperature was raised to 100° C. and the mixture was stirred overnight. The reaction mixture was quenched with brine and extracted with ethyl acetate (4×15 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulphate, filtrated and evaporated to give the crude product. Flash chromatography (ethyl acetate/heptane as eluent) gave (4-chloro-phenyl)-(6-pyrazol-1-yl-pyrazin-2-yl)-amine (56 mg, 27%) as a yellow solid.
Workup
- temperatureThe temperature was raised to 100° C.
- stirringthe mixture was stirred overnight
- customThe reaction mixture was quenched with brine
- extractionextracted with ethyl acetate (4×15 mL)
- washThe combined organic phases were washed with brine
- dry with materialdried over anhydrous sodium sulphate
- filtrationfiltrated
- customevaporated
- customto give the crude product
Sources & evidence
- ORD record
- ord-a2f824007755408c8515c2b29997c49b
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415358B2
Reaction notes
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