Triethylamine → HCID 87282652, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH3:9].CCN(CC)CC.[O:17]1[C:21]2[CH:22]=[CH:23][C:24]([C:26]3([C:29](Cl)=[O:30])[CH2:28][CH2:27]3)=[CH:25][C:20]=2[O:19][CH2:18]1>ClCCl>[O:17]1[C:21]2[CH:22]=[CH:23][C:24]([C:26]3([C:29]([NH:8][C:6]4[CH:5]=[CH:4][C:3]([CH3:9])=[C:2]([Cl:1])[N:7]=4)=[O:30])[CH2:27][CH2:28]3)=[CH:25][C:20]=2[O:19][CH2:18]1Participants
Procedure
To a solution of 6-chloro-5-methylpyridin-2-amine (71 mg, 0.50 mmol) and Et3N (140 μL, 1.0 mmol) in dichloromethane (2 mL) was added a solution of 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (110 mg, 0.50 mmol) in dichloromethane (2 mL). The resulting reaction mixture was allowed to stir at room temperature for 18 hours. The reaction mixture was then washed with 1N aqueous HCl (1×5 mL) and saturated aqueous NaHCO3 (1×5 mL). The organic layer was dried over sodium sulfate and evaporated to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(6-chloro-5-methylpyridin-2-yl)cyclopropanecarboxamide (120 mg, 71% over 2 steps). 1H NMR (400 MHz, DMSO-d6) δ 8.64 (s, 1H), 7.94-7.91 (m, 1H), 7.79-7.77 (m, 1H), 7.09 (m, 1H), 7.00-6.88 (m, 2H), 6.06 (s, 2H), 2.25 (s, 3H), 1.47-1.44 (m, 2H), 1.13-1.10 (m, 2H) ESI-MS m/z calc. 330.1. found 331.5 (M+1)+. Retention time 1.99 minutes.
Workup
- customThe resulting reaction mixture
- washThe reaction mixture was then washed with 1N aqueous HCl (1×5 mL) and saturated aqueous NaHCO3 (1×5 mL)
- dry with materialThe organic layer was dried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-3af9923c12ec46348e9ed2f7140abc45
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969386B2
Reaction notes
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