1-Pyrrolidineethanamine → HCID 86732796、化合物

HRID 525928ノート

反応式

HRID 525928 の反応式
[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:37])[C:5]([C:34](O)=[O:35])=[N:6][N:7]2[CH2:32][CH3:33].C(N(CC)CC)C.ClC(OCC(C)C)=O.[N:53]1([CH2:58][CH2:59][NH2:60])[CH2:57][CH2:56][CH2:55][CH2:54]1>O1CCCC1>[Cl:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:37])[C:5]([C:34]([NH:60][CH2:59][CH2:58][N:53]1[CH2:57][CH2:56][CH2:55][CH2:54]1)=[O:35])=[N:6][N:7]2[CH2:32][CH3:33]

参加物

6

反応物 4

HCID 13441-PyrrolidineethanamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 86732795HCID 86732795、化合物

生成物 1

HCID 86732796HCID 86732796、化合物収率 33.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid (3 g, 5.71 mmol) in tetrahydrofuran (THF) (25 mL) was added triethylamine (0.876 mL, 6.29 mmol), followed by isobutyl chloroformate (0.826 mL, 6.29 mmol). The reaction mixture was stirred at 0° C. for 30 min. 2-(Pyrrolidin-1-yl)ethanamine (0.979 g, 8.57 mmol) was added and the mixture was stirred at 0° C. for 30 min and warmed up to room temperature for 2 h. Solvent was removed and the residue was chromatographed to afford 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydrocinnoline-3-carboxamide (1.2 g, 1.932 mmol, 33.8% yield). LCMS: (M+H)+: 621.2

後処理

  1. stirringthe mixture was stirred at 0° C. for 30 min
  2. temperaturewarmed up to room temperature for 2 h
  3. customSolvent was removed
  4. customthe residue was chromatographed

出典と根拠

ORDレコード
ord-a604e812734c430f9815b2988f7e8052
出典データセット
uspto-grants-2016_05
特許番号
US09340556B2

反応ノート

読み込み中…