Nicotinic acid, hydrazide → 2-phenyl-5-(5-(pyridin-3-yl)-1H-1,2,4-triazol-3-yl)pyrimidine

HRID 42308

反応式

HRID 42308 の反応式
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([NH:23][NH2:24])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1>CC1C=CC=CC=1C.ClCCl.CO>[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[NH:23][N:24]=3)=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 2

HCID 11112Nicotinic acid, hydrazideHCID 140043942-Phenylpyrimidine-5-carbonitrile

生成物 1

HCID 592524612-phenyl-5-(5-(pyridin-3-yl)-1H-1,2,4-triazol-3-yl)pyrimidine収率 10%

試薬・触媒・溶媒 2

HCID 7237O-Xylene溶媒2 回HCID 21226129Dichloromethane methanol溶媒

実験手順

2-Phenyl-pyrimidine-5-carbonitrile (Biofine International, 0.20 g, 1.10 mmol) and nicotinic hydrazide (Aldrich, 0.151 g, 1.10 mmol) were dissolved in o-xylene (5 mL) and heated to 200° C. under nitrogen atmosphere for seven hours as the o-xylene slowly boiled off. The remaining crude solid was dissolved in a minimal amount of 98:2 v/v dichloromethane-methanol and purified by flash silica column chromatography. Elution through a 40-g Analogix® flash silica cartridge with 100% dichloromethane to 5% methanol in dichloromethane afforded the title compound as a yellow solid (32 mg, 10% yield); Rf 0.27 with 95:5 v/v dichloromethane-methanol; melting point 322-333° C.; 1H-NMR (400 MHz; CDCl3) δ 9.53 (s, 2H), 9.32 (d, 1H), 8.76-8.75 (m, 1H), 8.53-8.46 (m, 3H), 7.64-7.60 (m, 4H); MS (ESI+) m/z 301.1 (M+1); H-PGDS FPBA IC50: 1 μM.

後処理

  1. custompurified by flash silica column chromatography
  2. washElution through a 40-g Analogix® flash silica cartridge with 100% dichloromethane to 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-f281d796030e422b877137034544b3f4
出典データセット
uspto-grants-2013_09
特許番号
US08536185B2

関連ノート

読み込み中…