1-Hydroxybenzotriazole → N-(4-(7-(Benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorophenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 15516ノート

反応式

HRID 15516 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=O)[C:9]2=[O:17])=[CH:4][CH:3]=1.[CH:18]1[CH:19]=[CH:20][C:21]2N(O)N=N[C:22]=2[CH:23]=1.CCN=C=NCCCN(C)C.Cl.[CH3:40][O:41][C:42]1[CH:43]=[C:44]2[C:49](=[CH:50][C:51]=1[O:52][CH3:53])[N:48]=[CH:47][CH:46]=[C:45]2[O:54][C:55]1[CH:60]=[CH:59][C:58]([NH2:61])=[CH:57][C:56]=1[F:62]>CN(C=O)C>[CH2:53]([O:52][C:51]1[CH:50]=[C:49]2[C:44]([C:45]([O:54][C:55]3[CH:60]=[CH:59][C:58]([NH:61][C:14]([C:10]4[C:9](=[O:17])[N:8]([C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=5)[CH:13]=[CH:12][CH:11]=4)=[O:16])=[CH:57][C:56]=3[F:62])=[CH:46][CH:47]=[N:48]2)=[CH:43][C:42]=1[O:41][CH3:40])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineHCID 210815271-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

生成物 1

HCID 58833040N-(4-(7-(Benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorophenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide収率 64.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a mixture of 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (74 mg, 0.32 mmol), HOBt (16 mg) and EDCI.HCl (65 mg, 0.34 mmol) in DMF (3 mL) was added a solution of 4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorobenzenamine (120 mg, 0.31 mmol) in DMF (3 mL) at rt, and the reaction mixture was stirred overnight at rt. It was directly purified by preparative HPLC to afford the product (46 mg, 20%) as a white TFA salt solid. 1H NMR (DMF-d7) δ 12.22 (s, 1H), 8.71 (d, 1H, J=6.0 Hz), 8.59 (d, 1H, J=7.2 Hz), 8.14-7.31 (m, 15H), 6.84 (d, 1H, J=5.5 Hz), 6.72 (t, 1H, J=7.2 Hz), 5.35 (s, 2H), 4.02 (s, 3H); MS(ESI+) m/z 606.3 (M+H)+.

後処理

  1. customIt was directly purified by preparative HPLC

出典と根拠

ORDレコード
ord-21800dd0b62449349295126bfd11879b
出典データセット
uspto-grants-2010_06
特許番号
US07732613B2

反応ノート

読み込み中…