Diisopropylethylamine → 2-[(2-Aminocyclopentyl)methylamino]-4-methoxyquinoline

HRID 430081

반응식

HRID 430081 반응식
[NH2:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][NH2:8].Cl[C:10]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.CCN(C(C)C)C(C)C>CO>[NH3:1].[NH2:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][NH:8][C:10]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 89512Cyclopentanemethanamine, 2-amino-HCID 123691662-Chloro-4-methoxyquinoline

생성물 2

HCID 222AmmoniaHCID 183537542-[(2-Aminocyclopentyl)methylamino]-4-methoxyquinoline수율 16%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(2-Aminocyclopentyl)methylamine (0.50 g, 0.00438 mol), 2-chloro-4-methoxyquinoline (0.85 g, 0.00438 mol) and N,N′-diisopropylethylamine (1 ml) were stirred together at 80° C. in a sealed tube for 16 h. After cooling the mixture was diluted in methanol then concentrated onto silica gel and purified by silica gel chromatography (5%, 10% then 20% (10% 880 aqueous ammonia in methanol) in dichloromethane) to give the title compound as a white gum (50:50 mixture of cis and trans isomers; 0.095 g, 8%). δH (CD3OD) 1.40-2.25 (7H, m, (CH2)3, CHCH2NH), 2.96-3.76 (3H, m, CHNH2, CH2NH), 4.02 (3H, s, OCH3), 6.02-6.23 (1H, 2s, 3-H), 7.13-7.95 (4H, m, ArH). MS (ES+) 272 (M+H).

후처리

  1. temperatureAfter cooling the mixture
  2. concentrationthen concentrated onto silica gel
  3. custompurified by silica gel chromatography (5%, 10%

출처 및 근거

ORD 기록
ord-c9f95cfaedb74bd2812cae285ba83df0
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06320051B1

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