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

HRID 2079971ノート

反応式

HRID 2079971 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 81531Diisopropylethylamine溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b1570c3853654678a6e59cfb477bbc07
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

反応ノート

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