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Acetone → 6-Acetyl-2-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080198
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HRID 2080198 반응식
[NH2:1][C:2]1[N:23]=[C:22]([C:24]([O:26]CC)=[CH2:25])[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].CC(C)=O.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[C:24]([C:22]1[CH:21]=[CH:20][C:3]([C:4]([NH:6][CH2:7][C:8]2[S:9][C:10]([O:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:11][CH:12]=2)=[O:5])=[C:2]([NH2:1])[N:23]=1)(=[O:26])[CH3:25]
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참가 물질

7

반응물 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 231303892-Amino-6-(1-ethoxyvinyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

생성물 1

HCID 231304466-Acetyl-2-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide수율 53%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 2-amino-6 (1-ethoxy vinyl)-N-(5-phenoxy-thiophene-2-ylmethyl)-nicotinamide described in Preparation Example A+-14 (2.0 mg, 0.0051 mmol) and acetone (2 mL) were added water (1 mL) and concentrated sulfuric acid (0.2 mL), and the solution was stirred at room temperature for 3 hours. The reaction solution was neutralized with an aqueous solution of saturated sodium bicarbonate, and ethyl acetate was added for extraction. The organic layer was washed with brine, the solvent was then evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1), and the title compound (1.0 mg, 0.0027 mmol, 53%) was obtained as a white solid.

후처리

  1. additionwas added for extraction
  2. washThe organic layer was washed with brine
  3. customthe solvent was then evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-90b674e9cd6341f290d3d861cf6a5021
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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