Diethyl Pyrocarbonate → 2-[(4-fluorophenyl)sulfonyl-methyl-amino]-N-[[2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]prop-2-enamide

HRID 1479882ノート

反応式

HRID 1479882 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:17])[C:12](=[CH2:16])[C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCOC(OC(OCC)=O)=O.[F:29][C:30]([F:46])([F:45])[C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[C:41]([CH2:43][NH2:44])[CH:40]=[CH:39][N:38]=2)=[CH:33][CH:32]=1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH3:17])[C:12](=[CH2:16])[C:13]([NH:44][CH2:43][C:41]2[CH:40]=[CH:39][N:38]=[C:37]([C:34]3[CH:35]=[CH:36][C:31]([C:30]([F:46])([F:29])[F:45])=[CH:32][CH:33]=3)[CH:42]=2)=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 3051Diethyl PyrocarbonateHCID 68758847[2-(4-Trifluoromethyl-phenyl)-pyridin-4-yl]methylamineHCID 1317365812-[(4-Fluorophenyl)sulfonyl-methyl-amino]prop-2-enoic acid

生成物 1

HCID 783199102-[(4-fluorophenyl)sulfonyl-methyl-amino]-N-[[2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]prop-2-enamide収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of acid 4A (260 mg, 1 mmol) in THF (25 mL) was added with DEPC (0.18 mL, 1.3 mol eq) and the mixture was stirred at room temperature for about 5 minutes. Then [2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine 21A (1.1 equiv., 277.5 mg) was added. The reaction mixture was then stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was suspended in EtOAc (30 mL) and washed with water (50 mL) and brine. The separated organic phase, after anhydrification over Na2SO4, was evaporated under reduced pressure and the residue was purified by flash chromatography (1:1 EtOAc:Petroleum ether) to afford a pale yellow solid (100 mg) after crystallization from a mixture of diethyl ether/petroleum ether. Yield=49%, 1HNMR (DMSO, 400 MHz) δ 2.93 (3H, s), 4.48 (d, 2H, J=6 Hz), 5.08 (s, 1H), 5.87 (s, 1H), 7.35 (d, 1H), 7.37 (t, 2H, J=8.8 Hz), 7.82 (m, 4H), 8.03 (s, 1H), 8.28 (d, 2H, J=8.4 Hz), 8.63 (d, 1H, J=5.2 Hz), 8.95 (bt, 1H); [M+1] 494.47 (C23H19F4N3O3S requires 493.47).

後処理

  1. stirringThe reaction mixture was then stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. washwashed with water (50 mL) and brine
  4. customThe separated organic phase, after anhydrification over Na2SO4, was evaporated under reduced pressure
  5. customthe residue was purified by flash chromatography (1:1 EtOAc:Petroleum ether)

出典と根拠

ORDレコード
ord-e377c2f9315f4fdbb1f1d8d42c1d506b
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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