ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Ammonium nitrate → 2-(3-Amino-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

HRID 1599089
ノート
印刷プレビュー

反応式

HRID 1599089 の反応式
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([N:13]([CH:22]([CH3:24])[CH3:23])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:12])[C:6]2[CH:25]=[CH:26][CH:27]=[CH:28][C:5]=2[N:4](CC2C=CC(OC)=CC=2)[C:3]1=[O:38].[N+]([O-])([O-])=O.[NH4+]>C(#N)C.O>[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([N:13]([CH:22]([CH3:24])[CH3:23])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:12])[C:6]2[CH:25]=[CH:26][CH:27]=[CH:28][C:5]=2[NH:4][C:3]1=[O:38]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 22985Ammonium nitrateHCID 189295902-[3-Amino-5-(4-methoxybenzyl)-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)-acetamide

生成物 1

HCID 189295732-(3-Amino-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide収率 97.6%

試薬・触媒・溶媒 1

HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

To a stirred solution of 2-[3-Amino-5-(4-methoxybenzyl)-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)-acetamide (2.63 g, 5.09 mmol) in acetonitrile/H2O (9:1, 70 mL) at ambient temperature was added cerric ammonium nitrate (10.05 g, 18.3 mmol) portionwise over one hour. The solution was stirred overnight at room temperature. The solution was concentrated in vacuo, chased with toluene (2×50 mL) and the residue was extracted with CH2Cl2 (3×50 mL), filtered and concentated to an orange glass. The crude product was purified by flash chromatography on silica gel (100 g) eluting successively with CH2 Cl2 /CH3OH (15:1, 1.5 L) and CH2Cl2 /CH3OH (10:1, 1.3 L). Appropriate fractions were combined and concentrated under reduced pressure to give the title compound (1.97 g, 4.97 mmol) as a brown foam: 1H NMR (300 MHz, DMSO-d6): d 10.68 (br s, 1H), 7.39-6.98 (m, 8H), 5.75 (s, 1H), 4.76 (m, 1H), 4.16-3.92 (m, 4H), 3.7 (s, 3H), 3.15 (m, 2H), 0.97 (m, 6H); TLC (CH2Cl2 /CH3OH (13:1)): Rf =0.21.

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. extractionthe residue was extracted with CH2Cl2 (3×50 mL)
  3. filtrationfiltered
  4. customThe crude product was purified by flash chromatography on silica gel (100 g)
  5. washeluting successively with CH2 Cl2 /CH3OH (15:1, 1.5 L) and CH2Cl2 /CH3OH (10:1, 1.3 L)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d071d168adaf4af0b784dd036badba19
出典データセット
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05739129

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート