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(3-Methoxyphenyl)acetic acid → N-(4-(1H-pyrrolo[2,3-b]pyridin-3-yl)thiophen-2-yl)-2-(3-methoxyphenyl)acetamide

HRID 2108749
ノート
印刷プレビュー

反応式

HRID 2108749 の反応式
C1(C)C=CC(S(N2C3=NC=CC=C3C(C3C=C(N)SC=3)=C2)(=O)=O)=CC=1.COC1C=C(CC(O)=O)C=CC=1.[CH3:38][O:39][C:40]1[CH:41]=[C:42]([CH2:46][C:47]([NH:49][C:50]2[S:51][CH:52]=[C:53]([C:55]3[C:63]4[C:58](=[N:59][CH:60]=[CH:61][CH:62]=4)[N:57](S(C4C=CC(C)=CC=4)(=O)=O)[CH:56]=3)[CH:54]=2)=[O:48])[CH:43]=[CH:44][CH:45]=1.O[Li].O>C1COCC1.O.CCOC(C)=O>[NH:57]1[C:58]2=[N:59][CH:60]=[CH:61][CH:62]=[C:63]2[C:55]([C:53]2[CH:54]=[C:50]([NH:49][C:47](=[O:48])[CH2:46][C:42]3[CH:43]=[CH:44][CH:45]=[C:40]([O:39][CH3:38])[CH:41]=3)[S:51][CH:52]=2)=[CH:56]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

8

反応物 4

HCID 15719(3-Methoxyphenyl)acetic acidHCID 168937Lithium hydroxide, monohydrateHCID 576330322-Thiophenamine, 4-[1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl]-HCID 576332172-(3-methoxyphenyl)-N-(4-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophen-2-yl)acetamide

生成物 1

HCID 11595702N-(4-(1H-pyrrolo[2,3-b]pyridin-3-yl)thiophen-2-yl)-2-(3-methoxyphenyl)acetamide
収率 39.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

4-[1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-thiophen-2-ylamine was coupled to 3-methoxyphenylacetic acid according to General Method B and the product 2-(3-methoxyphenyl)-N-(4-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophen-2-yl)acetamide (70 mg, 0.14 mmol) was dissolved in 6 mL THF and LiOH hydrate (63 mg, 1.5 mmol) was added in 1 mL of water. The reaction mixture was heated to 150° C. by microwave irradiation for 15 minutes and then diluted with EtOAc and water and the organic layer dried over sodium sulfate and concentrated to an oil, which was purified by column chromatography on silica (40 to 100% EtOAc/hexanes to give 20 mg of a light brown solid, 0.055 mmol, 39%. 1H NMR 500 MHz (DMSO-d6) 11.80 (1H, s), 11.37 (1H, s) 8.28 (2H, m), 7.78 (1H, s), 7.25 (1H, t), 7.16 (2H, m), 7.07 (1H, s) 6.88 (2H, m), 6.82 (1H, m), 3.78 (3H, s), 3.69 (2H, s). MH+ 364.20.

後処理

  1. dry with materialthe organic layer dried over sodium sulfate
  2. concentrationconcentrated to an oil, which
  3. customwas purified by column chromatography on silica (40 to 100% EtOAc/hexanes

出典と根拠

ORDレコード
ord-c305b37ca2a549e591717cc0c0b8d273
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07514448B2

反応ノート

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