1-Phenethylamine → 3-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one

HRID 1014716ノート

反応式

HRID 1014716 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:5]([N+:17]([O-])=O)=[CH:4][CH:3]=1.Cl[C:21]1[C:26]([N+]([O-])=O)=[CH:25][CH:24]=[C:23](Cl)[N:22]=1.C(N(C(C)C)CC)(C)C.[C:40]1(C(N)C)C=C[CH:43]=[CH:42][CH:41]=1.[O:49]1CCC[CH2:50]1>>[C:11]1([CH:9]([N:8]2[C:6]3=[N:7][C:2]([C:43]4[CH:42]=[CH:41][CH:40]=[C:21]5[C:26]=4[CH:25]=[CH:24][CH:23]=[N:22]5)=[CH:3][CH:4]=[C:5]3[NH:17][C:50]2=[O:49])[CH3:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

6

反応物 5

HCID 74081-PhenethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 433303216-chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amine

生成物 1

HCID 249846803-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one収率 78%

反応条件

温度
-78 °C

実験手順

6-Chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amine. To a solution of 2,6-dichloro-3-nitropyridine (2.0 g, 10.4 mmol) in tetrahydrofuran (18 mL) at −78° C. was added diisopropylethylamine (2.17 mL, 12.4 mmol) and 1-phenylethanamine (1.51 g, 12.4 mmol). The reaction was maintained at −78° C. for 2 h and then allowed to slowly warm to room temperature overnight. Solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to afford the title compound (2.24 g, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.68 (d, J=7.5, 1H), 8.42 (d, J=8.5, 1H), 7.45 (d, J=7.5, 2H), 7.34 (t, J=7.5, 2H), 7.25 (t, J=7.5, 1H), 6.80 (d, J=8.5, 1H), 5.36 (app quint, J=7, 1H), 1.57 (d, J=7, 3H).

後処理

  1. temperatureto slowly warm to room temperature overnight
  2. customSolvent was removed under reduced pressure
  3. customthe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-6ff5800ff6254a87b7f2038ae20ef298
出典データセット
uspto-grants-2011_07
特許番号
US07981893B2

反応ノート

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