Triethylamine → 4-[[2-(5-Bromo-2-fluorophenyl)pteridin-4-yl]amino]nicotinic Acid Methyl Ester

HRID 928265

反応式

HRID 928265 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]2[N:17]=[C:16](Cl)[C:15]3[C:10](=[N:11][CH:12]=[CH:13][N:14]=3)[N:9]=2)[CH:7]=1.[CH3:20][O:21][C:22](=[O:30])[C:23]1[C:28]([NH2:29])=[CH:27][CH:26]=[N:25][CH:24]=1.C(N(CC)CC)C>ClC(Cl)C>[CH3:20][O:21][C:22](=[O:30])[C:23]1[C:28]([NH:29][C:16]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][N:14]=3)[N:9]=[C:8]([C:6]3[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[F:19])[N:17]=2)=[CH:27][CH:26]=[N:25][CH:24]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 592353Methyl 4-aminopyridine-3-carboxylateHCID 577423812-(5-Bromo-2-fluorophenyl)-4-Chloropteridine

生成物 1

HCID 577423794-[[2-(5-Bromo-2-fluorophenyl)pteridin-4-yl]amino]nicotinic Acid Methyl Ester収率 74.6%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

反応条件

温度
70 °C

実験手順

To a solution of 2-(5-bromo-2-fluorophenyl)-4-chloropteridine 106 (200 mg, 0.589 mmol), 4-aminonicotinic acid methyl ester (224 mg, 1.47 mmol) in dichloroethane (5 mL), was added dropwise triethylamine (300 μL, 2.07 mmol). The resulting mixture was heated at 70° C. for 15 min, then quenched with silica and purified by column chromatography (AcOEt/CH2Cl2/triethylamine, 70/19/1). Crystallization from AcOEt/Et2O afforded 200 mg of the title product 107 as yellow prisms (LCMS analysis).

後処理

  1. customquenched with silica
  2. custompurified by column chromatography (AcOEt/CH2Cl2/triethylamine, 70/19/1)
  3. customCrystallization from AcOEt/Et2O

出典と根拠

ORDレコード
ord-9114b28750b041699f72acfb20787d81
出典データセット
uspto-grants-2016_03
特許番号
US09290502B2

関連ノート

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