Ammonia → 1-(6-Chloro-3-pyridinyl)cyclopropanecarboxamide
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.C([N:24](CC)CC)C.N>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([NH2:24])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a 0° C. solution of 1-(6-chloropyridin-3-yl)cyclopropanecarboxylic from Step 4 (1.0 g) in chloroform (50 mL) were slowly added isobutyl chloroformate (800 μL) and triethylamine (920 μL). The reaction mixture was stirred at 0° C. for 2 hours. Then it was saturated with ammonia gas and stirred at 0° C. for 10 minutes. The reaction mixture was allowed to stand at room temperature for 1 hour then poured into water (80 mL) and partitioned. The aqueous layer was extracted with dichloromethane (2×80 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound.
Workup
- customTo a 0° C.
- stirringstirred at 0° C. for 10 minutes
- waitto stand at room temperature for 1 hour
- custompartitioned
- extractionThe aqueous layer was extracted with dichloromethane (2×80 mL)
- washThe combined extracts were washed with brine
- dry with materialdried with magnesium sulfate
- customthe solvent removed in vacuo
- customThe residue was purified
Sources & evidence
- ORD record
- ord-d2390e9d5fcb4aec8f8717a51dfac4ca
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687524B2
Reaction notes
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