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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
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HRID 2108749 반응식
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
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8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c305b37ca2a549e591717cc0c0b8d273
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07514448B2

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