Oxalyl chloride → 6-Chloro-N-(4-ethoxyquinolin-8-yl)-2-fluoro-3-(pivalamidomethyl)benzamide

HRID 1469849ノート

反応式

HRID 1469849 の反応式
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[C:9]([NH2:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1)[CH3:2].[Cl:15][C:16]1[C:21]([C:22](O)=[O:23])=[C:20]([F:25])[C:19]([CH2:26][NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:18][CH:17]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:15][C:16]1[C:21]([C:22]([NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:8]=2[N:7]=[CH:6][CH:5]=[C:4]3[O:3][CH2:1][CH3:2])=[O:23])=[C:20]([F:25])[C:19]([CH2:26][NH:27][C:28](=[O:33])[C:29]([CH3:31])([CH3:30])[CH3:32])=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 682812844-Ethoxyquinolin-8-amine

生成物 1

HCID 866923026-Chloro-N-(4-ethoxyquinolin-8-yl)-2-fluoro-3-(pivalamidomethyl)benzamide収率 23.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

The title compound was prepared following the procedure described in Example-1 using 4-ethoxyquinolin-8-amine (Intermediate-56, 80 mg, 0.425 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 159 mg, 0.553 mmol), oxalyl chloride (162 mg, 1.27 mmol), DMF (1 drop) and DIPEA (219 mg, 1.7 mmol) in CH2Cl2 (2 mL) to afford 46 mg of the title product. 1H NMR (400 MHz, DMSO-d6): δ 10.59 (s, 1H), 8.71-8.68 (m, 2H), 8.13 (t, 1H), 7.93-7.90 (dd, J=1.2, 8.4 Hz, 1H), 7.61-7.57 (t, J=8.0 Hz, 1H), 7.42-7.40 (d, J=8.4 Hz, 1H), 7.36-7.23 (t, J=8.0 Hz, 1H), 7.12-7.11 (d, J=5.2 Hz, 1H), 4.35-4.29 (m, 4H), 1.50-1.47 (t, J=7.2 Hz, 3H), 1.14 (s, 9H); MS (m/z): 458.24 (M+H)+.

後処理

  1. customThe title compound was prepared

出典と根拠

ORDレコード
ord-52ea0922ee4b46169e739d5c04924617
出典データセット
uspto-grants-2015_04
特許番号
US09006257B2

反応ノート

読み込み中…