Diisopropylethylamine → N-{5-bromo-2-[(pyridin-2-ylcarbonyl)amino]benzyl}pyridine-2-carboxamide

HRID 1786776ノート

反応式

HRID 1786776 の反応式
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:4]=1[NH:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:12].C(N(CC)C(C)C)(C)C.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](Cl)=[O:35]>C(Cl)Cl>[Br:9][C:7]1[CH:6]=[CH:5][C:4]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:12])=[C:3]([CH:8]=1)[CH2:2][NH:1][C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=1)=[O:35]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 57598296N-[2-(aminomethyl)-4-bromophenyl]pyridine-2-carboxamide

生成物 1

HCID 11212049N-{5-bromo-2-[(pyridin-2-ylcarbonyl)amino]benzyl}pyridine-2-carboxamide収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Compound 2-3 (0.050 g, 0.16 mmoles) was dissolved in 6 mL of methylene chloride. To the reaction vessel was added (0.06 mL, 0.32 mmoles) of N,N-diisopropylethylamine and (200 mg, 0.32 mmols, 1.49 mmol/gram) followed by the addition of (0.057 g, 0.32 mmol) picolinoyl chloride. The mixture was stirred until complete by TLC. The compound was then filtered and then the solvent was removed and then purified on a mass guided LC/MS to provide 46 mg (70%) of the title compound. 1H NMR (300 MHz, CDCl3): 8.89 ppm (s, 2H), 8.43 ppm (m, 2H), 8.22 ppm (m, 2H), 8.13 ppm (t, J=4 Hz, 1H), 8.0 ppm (s, 1H), 7.81 ppm (m, 2H), 7.41 ppm (m, 1H), 7.2 ppm (m, 2H), 4.22 ppm (d, J=4 Hz, 2H); HRMS calc'd for C19H15BrN4O2 (M+1) 411.0451; Found: 411.0444

後処理

  1. filtrationThe compound was then filtered
  2. customthe solvent was removed
  3. custompurified on a mass

出典と根拠

ORDレコード
ord-583ff380a4bf48fc946d55bf26c23e13
出典データセット
uspto-grants-2009_03
特許番号
US07507836B2

反応ノート

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