Ethanolamine → 2-Amino-6-(2-hydroxy-ethylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080206ノート

反応式

HRID 2080206 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].C1C=CC(CC(NC[NH:36][C@H:37]([C:48](O)=[O:49])CC2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1.C(CN)O>CS(C)=O.C(N(C(C)C)CC)(C)C.[Cl-].[Na+].O>[NH2:1][C:2]1[N:23]=[C:22]([NH:36][CH2:37][CH2:48][OH:49])[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

7

反応物 3

HCID 700EthanolamineHCID 188218A-101HCID 231304982-aminochloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

生成物 1

HCID 231306602-Amino-6-(2-hydroxy-ethylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide収率 76%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 81531Diisopropylethylamine溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
135 °C

実験手順

2-Amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-101 (170 mg, 0.47 mmol) was dissolved in a mixture solution of dimethylsulfoxide (2 mL) and diisopropylethylamine (1 mL), ethanolamine (0.428 mL, 7.1 mmol) was added thereto, followed by heating in a sealed tube for 15 hours 20 minutes (oil bath temperature: 135° C.). The reaction mixture was allowed to room temperature, poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=2:1), and the title compound (138 mg, 0.36 mmol, 76%) was obtained.

後処理

  1. additionwas added
  2. customwas allowed to room temperature
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customthe obtained residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=2:1)

出典と根拠

ORDレコード
ord-27da6187de6444f49f74e91c20c03224
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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