Trifluoroacetic acid → Quinoline-6-carboxylic acid (5-(3-hydroxy-phenoxy)-thiophen-2-ylmethyl)-amide

HRID 2080247

반응식

HRID 2080247 반응식
FC(F)(F)C(O)=O.C([O:15][C:16]1[CH:17]=[C:18]([CH:39]=[CH:40][CH:41]=1)[O:19][C:20]1[S:24][C:23]([CH2:25][NH:26][C:27]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][CH:33]=[CH:32]3)=[O:28])=[CH:22][CH:21]=1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1(SC)C=CC=CC=1>[OH:15][C:16]1[CH:17]=[C:18]([CH:39]=[CH:40][CH:41]=1)[O:19][C:20]1[S:24][C:23]([CH2:25][NH:26][C:27]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][CH:33]=[CH:32]3)=[O:28])=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67119634Quinoline-6-carboxylic acid (5-(3-benzyloxy-phenoxy)-thiophen-2-ylmethyl)-amide

생성물 1

HCID 58387979Quinoline-6-carboxylic acid (5-(3-hydroxy-phenoxy)-thiophen-2-ylmethyl)-amide수율 80%

시약·촉매·용매 1

HCID 7520Thioanisole용매

실험 절차

Trifluoroacetic acid (1.0 mL) and thioanisole (100 μl) were added to the resulting quinoline-6-carboxylic acid (5-(3-benzyloxy-phenoxy)-thiophene-2-ylmethyl)-amide (73 mg, 0.156 mmol), and the solution was stirred for 30 minutes at room temperature. The reaction solution was neutralized with an aqueous solution of saturated sodium bicarbonate, then, extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (ethyl acetate: methanol), and the title compound (47 mg, 80%) was obtained as a colorless solid.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by NH silica gel column chromatography (ethyl acetate: methanol)

출처 및 근거

ORD 기록
ord-e005000e92794df68982b8121a740061
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

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