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Diethyl Ether → N-(4-((2-(cyclopropanecarboxamido)pyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide methanesulfonate

HRID 1411148
ノート
印刷プレビュー

反応式

HRID 1411148 の反応式
[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([F:20])=[CH:18][C:17]([NH:21][C:22]([C:24]4[C:25](=[O:40])[N:26]([C:33]5[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=5)[CH:27]=[CH:28][C:29]=4[O:30][CH2:31][CH3:32])=[O:23])=[C:16]([F:41])[CH:15]=3)[CH:10]=[CH:9][N:8]=2)=[O:5])[CH2:3][CH2:2]1.[CH3:42][S:43]([OH:46])(=[O:45])=[O:44].CCOCC>CC#N>[CH3:42][S:43]([OH:46])(=[O:45])=[O:44].[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([F:20])=[CH:18][C:17]([NH:21][C:22]([C:24]4[C:25](=[O:40])[N:26]([C:33]5[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=5)[CH:27]=[CH:28][C:29]=4[O:30][CH2:31][CH3:32])=[O:23])=[C:16]([F:41])[CH:15]=3)[CH:10]=[CH:9][N:8]=2)=[O:5])[CH2:3][CH2:2]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 71575771N-(4-((2-(cyclopropanecarboxamido)pyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

生成物 1

HCID 86703362N-(4-((2-(cyclopropanecarboxamido)pyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide methanesulfonate収率 44.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

A suspension of N-(4-((2-(cyclopropanecarboxamido)pyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (0.029 g, 0.051 mmol) in MeCN (0.5 mL) was heated to 80° C., treated with methanesulfonic acid (3.34 μl, 0.051 mmol), then cooled to RT and stirred overnight. Ether was added drop wise until solids precipitated. The mixture was stirred for several hours. The solids were collected by filtration, rinsed with ether and dried under vacuum to afford N-(4-((2-(cyclopropanecarboxamido)pyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide methanesulfonate (15 mg, 44% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.22 (s, 1H), 10.99 (s, 1H), 8.33 (dd, J=12.6, 7.2 Hz, 1H), 8.20 (d, J=5.8 Hz, 1H), 7.92 (d, J=7.8 Hz, 1H), 7.63-7.45 (m, 4H), 7.36 (m, 2H), 6.79 (d, J=5.7 Hz, 1H), 6.55 (d, J=7.9 Hz, 1H), 4.28 (q, J=7.0 Hz, 2H), 2.29 (s, 3H), 1.93 (m, 1H), 1.33 (t, J=7.0 Hz, 3H), 0.77 (m, 4H); MS (ESI) m/z: 565.2 (M+H+).

後処理

  1. temperaturecooled to RT
  2. customprecipitated
  3. stirringThe mixture was stirred for several hours
  4. filtrationThe solids were collected by filtration
  5. washrinsed with ether
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-ababbdd8068f4a22a9e2d95f3388f1f5
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921565B2

反応ノート

読み込み中…

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