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Potassium Carbonate → N-(4-((2-acetamidopyridin-4-yl)oxy)-2,5-difluorophenyl)-1-(4-fluorophenyl)-4-isopropoxy-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 1050869
ノート
印刷プレビュー

反応式

HRID 1050869 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20]([C:22]3[C:23](=[O:38])[N:24]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH:25]=[CH:26][C:27]=3[O:28][CH2:29][CH3:30])=[O:21])=[C:14]([F:39])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[C:40]([O-])([O-])=O.[K+].[K+]>C(O)(C)C>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20]([C:22]3[C:23](=[O:38])[N:24]([C:31]4[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=4)[CH:25]=[CH:26][C:27]=3[O:28][CH:29]([CH3:40])[CH3:30])=[O:21])=[C:14]([F:39])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 71566461N-(4-((2-acetamidopyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

生成物 1

HCID 71575825N-(4-((2-acetamidopyridin-4-yl)oxy)-2,5-difluorophenyl)-1-(4-fluorophenyl)-4-isopropoxy-2-oxo-1,2-dihydropyridine-3-carboxamide収率 71.9%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A mixture of Example 1 (0.400 g, 0.743 mmol) and K2CO3 (0.400 g, 2.89 mmol) in isopropanol (10 mL) was heated at 120° C. for 1 h with microwave irradiation. The solids were removed by filtration and washed with THF. The filtrate was concentrated to dryness. The residue was stirred in water (15 mL) and the remaining solids were collected and crystallized from MeCN to provide N-(4-((2-acetamidopyridin-4-yl)oxy)-2,5-difluorophenyl)-1-(4-fluorophenyl)-4-isopropoxy-2-oxo-1,2-dihydropyridine-3-carboxamide, (0.295 g, 71.9% yield) as white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.03 (s, 1 H), 10.58 (s, 1 H), 8.29 (dd, J=12.6, 7.2 Hz, 1 H), 8.18 (d, J=5.7 Hz, 1 H), 7.87 (d, J=7.8 Hz, 1 H), 7.67 (s, 1 H), 7.50-7.49 (m, 3 H), 7.35 (t, J=8.7 Hz, 2 H), 6.71 (dd, J=5.7, 2.4 Hz, 1 H), 6.55 (d, J=7.9 Hz, 1 H), 4.85 (m, 1 H), 2.03 (s, 3 H), 1.31 (d, J=6.0 Hz, 6 H); MS (ESI) m/z: 553.1 (M+H+).

後処理

  1. customThe solids were removed by filtration
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated to dryness
  4. customthe remaining solids were collected
  5. customcrystallized from MeCN

出典と根拠

ORDレコード
ord-1b0377e60123433d888ec52254590b33
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09387202B2

反応ノート

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