Triethylamine → N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamide
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C(N(CC)CC)C.[F:17][C:18]1([F:33])[O:22][C:21]2[CH:23]=[CH:24][C:25]([C:27]3([C:30](Cl)=[O:31])[CH2:29][CH2:28]3)=[CH:26][C:20]=2[O:19]1>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:30]([C:27]2([C:25]3[CH:24]=[CH:23][C:21]4[O:22][C:18]([F:33])([F:17])[O:19][C:20]=4[CH:26]=3)[CH2:29][CH2:28]2)=[O:31])[CH:5]=[CH:4][C:3]=1[CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-chloro-5-methylpyridin-2-amine (11 g, 78 mmol) and triethylamine (22.0 mL, 156 mmol) in dichloromethane (100 mL) was added a solution of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (20.3 g, 78 mmol) in dichloromethane (50 mL). The resulting reaction mixture was allowed to stir at room temperature for eighteen hours. The reaction mixture was then washed with 1N aqueous NaOH (2×200 mL), 1 N aqueous HCl (1×200 mL) and saturated aqueous NaHCO3 (1×200 mL). The organics were dried over sodium sulfate and evaporated to yield the product (26.9 g, 73.3 mmol, 94% 2-step). ESI-MS m/z calc. 366.06, found 367.3 (M+1)+. Retention time 2.19 minutes. 1H NMR (400 MHz, DMSO-d6) δ 9.30 (s, 1H), 7.89-7.87 (m, 1H), 7.78-7.76 (m, 1H), 7.54-7.53 (m, 1H), 7.41-7.39 (m, 1H), 7.33-7.30 (m, 1H), 2.26 (s, 3H), 1.52-1.49 (m, 2H), 1.19-1.16 (m, 2H).
Workup
- customThe resulting reaction mixture
- washThe reaction mixture was then washed with 1N aqueous NaOH (2×200 mL), 1 N aqueous HCl (1×200 mL) and saturated aqueous NaHCO3 (1×200 mL)
- dry with materialThe organics were dried over sodium sulfate
- customevaporated
- customto yield the product (26.9 g, 73.3 mmol, 94% 2-step)
Sources & evidence
- ORD record
- ord-c585c88fee584704b1fbb0d6b7f3ae4b
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08227615B2
Reaction notes
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