Water → 2-Amino-6-(2-amino-ethylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2079971노트

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HRID 2079971 반응식
[NH2:1][C:2]1[N:23]=[C:22](Cl)[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].[CH2:25]([NH2:28])[CH2:26][NH2:27].O>CS(C)=O.C(N(CC)C(C)C)(C)C>[NH2:1][C:2]1[N:23]=[C:22]([NH:27][CH2:26][CH2:25][NH2:28])[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]

참가 물질

6

반응물 3

HCID 962WaterHCID 3301EthylenediamineHCID 231304982-aminochloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

생성물 1

HCID 231305652-Amino-6-(2-amino-ethylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide수율 60%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 81531Diisopropylethylamine용매

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온도
120 °C

실험 절차

2-Amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide (150 mg, 0.417 mmol) described in Preparation Example A+-11, ethane-1,2-diamine (418 μl, 6.25 mmol) were dissolved in a mixture solution of dimethylsulfoxide (2 mL) and N,N-diisopropylethylamine (1 mL), and the solution was stirred at 120° C. for 15 hours. The reaction solution was cooled to room temperature, water was added, then extracted with ethyl acetate and tetrahydrofuran, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, tetrahydrofuran and NH silica gel were added to the residue, the solvent was evaporated in vacuo adsorption, purification was carried out by NH silica gel column chromatography (ethyl acetate:methanol=10:1), and the title compound (95 mg, 0.25 mmol, 59%) was obtained as a white solid.

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate and tetrahydrofuran
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo, tetrahydrofuran and NH silica gel
  6. additionwere added to the residue
  7. customthe solvent was evaporated in vacuo adsorption, purification

출처 및 근거

ORD 기록
ord-b1570c3853654678a6e59cfb477bbc07
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

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