Triethylamine → HCID 87555366, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.CCN(CC)CC.[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]=[C:4]([CH3:9])[CH:3]=1Participants
Procedure
To a solution of 6-chloro-4-methylpyridin-2-amine (300 mg, 2.1 mmol) and Et3N (1.8 mL, 13 mmol) in dichloromethane (5 mL) was added a solution of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (1.6 g, 6.3 mmol) in dichloromethane (5 mL). The resulting reaction mixture was allowed to stir at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane (10 mL) and was washed with 1N aqueous HCl (1×20 mL) and saturated aqueous NaHCO3 (1×20 mL). The organics were dried over sodium sulfate and evaporated to dryness. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-70% ethyl acetate in hexane to yield N-(6-chloro-4-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (700 mg, 91%). ESI-MS m/z calc. 366.1. found 366.9 (M+1)+. Retention time 2.15 minutes.
Workup
- customThe resulting reaction mixture
- washwas washed with 1N aqueous HCl (1×20 mL) and saturated aqueous NaHCO3 (1×20 mL)
- dry with materialThe organics were dried over sodium sulfate
- customevaporated to dryness
- customThe resulting residue was purified by silica gel chromatography
- washeluting with a gradient of 0-70% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-11cbc8f844224e08aaee73f9417066f3
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969386B2
Reaction notes
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