2-Aminopyridine → HCID 86615861, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8](C1NC=CN=1)(C1NC=CN=1)=[S:9].[N:20]1([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C(Cl)Cl.C(OCC)C>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:8]([N:23]1[CH2:24][CH2:25][N:20]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][CH2:22]1)=[S:9]Participants
Conditions
- Temperature
- 25 °C
Procedure
Part A: To a solution of 2-aminopyridine (9.41 g, 100 mmol) in methylene chloride (200 mL) at 25° C. was added thiocarbonyl diimidazole (18.75 g, 100 mmol), and the resulting mixture was stirred at 25° C. for 20 h. To the reaction mixture then was added tert-butyl piperazine-1-carboxylate (18.60 g, 100 mmol), and the resulting mixture was stirred at 25° C. for another 24 h. The mixture was diluted with diethyl ether, washed with water (×3) and brine, dried over anhyd. sodium sulfate, filtered, and concentrated. Column chromatography on silica gel (elution: 0-20% diethyl ether/methylene chloride) to afford tert-butyl 4-(pyridin-2-ylcarbamothioyl)piperazine-1-carboxylate (13.60 g) as a colorless solid, following crystallization from a mixture of 1-chlorobutane/hexane; 1H NMR (300 MHz, CDCl3) δ 7.97 (m, 1H), 7.64 (m, 2H), 6.88 (m, 1H), 4.00 (m, 4H), 3.51 (m, 4H), 1.44 (s, 9H).
Workup
- stirringthe resulting mixture was stirred at 25° C. for another 24 h
- washwashed with water (×3) and brine
- customdried over anhyd
- filtrationsodium sulfate, filtered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3115e7224f3b41e09a538fe4924b62a4
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807676B2
Reaction notes
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