Diethyl Pyrocarbonate → 2-(methyl(p-tolylsulfonyl)amino)-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide

HRID 1479818ノート

反応式

HRID 1479818 の反応式
[CH3:1][N:2]([S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[C:3](=[CH2:7])[C:4]([OH:6])=O.CCOC(OC(OCC)=O)=O.[F:29][C:30]([F:47])([F:46])[O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[C:42]([CH2:44][NH2:45])[CH:41]=[CH:40][N:39]=2)=[CH:34][CH:33]=1>C1COCC1>[CH3:1][N:2]([S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[C:3](=[CH2:7])[C:4]([NH:45][CH2:44][C:42]1[CH:41]=[CH:40][N:39]=[C:38]([C:35]2[CH:34]=[CH:33][C:32]([O:31][C:30]([F:47])([F:29])[F:46])=[CH:37][CH:36]=2)[CH:43]=1)=[O:6]

参加物

5

反応物 3

HCID 3051Diethyl PyrocarbonateHCID 68759664[2-[4-(Trifluoromethoxy)phenyl]-4-pyridyl]methanamineHCID 903842282-(Methyl(p-tolylsulfonyl)amino)prop-2-enoic acid

生成物 1

HCID 903842092-(methyl(p-tolylsulfonyl)amino)-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide収率 25%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of acid 4E (0.57 g, 2.2 mmol) in THF (30 mL) was added with DEPC (0.43 mL, 1.3 mol eq) and the mixture was stirred at room temperature for about 5 minutes. Then [2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 21B (0.66 g, 1.1 mol eq) and a catalytic amount of TEA were added, then the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was suspended in EtOAc and washed with water and brine. The separated organic phase was evaporated under reduced pressure and the residue was purified by flash chromatography (7:3 EtOAc:Petroleum ether) to afford a pale yellow solid (0.27 g) after crystallization from a mixture of diethyl ether/petroleum ether. Yield=25%, 1HNMR (DMSO, 200 MHz) δ 2.48 (s, 3H), 2.86 (s, 3H), 4.49 (d, 2H, J=6), 5.00 (s, 1H), 5.85 (s, 1H), 7.35 (d, 1H), 7.42 (m, 4H), 7.71 (d, 2H, J=8.2), 7.97 (s, 1H), 8.21 (dd, 2H, J=2.2), 8.61 (d, 1H, J=4), 8.90 (t, 1H); [M+1] 505.51 (C24H22F3N3O4S requires 505.12).

後処理

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. washwashed with water and brine
  4. customThe separated organic phase was evaporated under reduced pressure
  5. customthe residue was purified by flash chromatography (7:3 EtOAc:Petroleum ether)

出典と根拠

ORDレコード
ord-4aad5fa7fe9e42939fc522c275eb8e65
出典データセット
uspto-grants-2016_08
特許番号
US09409864B2

反応ノート

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