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Sodium Hydroxide → 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid

HRID 1529221
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HRID 1529221 반응식
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][CH3:17])[C:11]=2[C:18]#[C:19][C:20]2[CH:21]=[N:22][C:23]([NH2:26])=[CH:24][CH:25]=2)=[CH:6][C:5]=1[O:27][CH3:28].[OH-].[Na+]>C1COCC1>[NH2:26][C:23]1[N:22]=[CH:21][C:20]([C:19]#[C:18][C:11]2[C:12]([CH2:16][CH3:17])=[N:13][CH:14]=[CH:15][C:10]=2[C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:29])=[O:2])=[C:5]([O:27][CH3:28])[CH:6]=2)=[CH:25][CH:24]=1
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 582353114-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid methyl ester

생성물 1

HCID 582352604-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The title compound is synthesized according to general procedure GP4 starting from 1.07 g (2.77 mmol) 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid methyl ester (A-41) using 2.4 mL (2.4 mmoL) 1N NaOH in 30 mL THF. The reaction mixture is stirred over night, after complete consumption of the starting material the pH is adjusted to 4 (using 1N HCl). As no precipitate is formed, the aqueous phase is extracted with DCM. However, the product precipitates upon addition of DCM and is collected by filtration. Additional product is precipitated from the mother liquid by adjustment of the pH to 6 (using 1N NaOH). Yield of the combined fractions: 990 mg (96%).

후처리

  1. customafter complete consumption of the starting material the pH
  2. customAs no precipitate is formed
  3. extractionthe aqueous phase is extracted with DCM
  4. customHowever, the product precipitates upon addition of DCM
  5. filtrationis collected by filtration
  6. customAdditional product is precipitated from the mother liquid by adjustment of the pH to 6 (using 1N NaOH)

출처 및 근거

ORD 기록
ord-774948f6910f496a81659d6a7779630d
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090564B2

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