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Ethyl 2-(quinolin-8-yloxy)acetate → (R)-N-(2-hydroxy-3-(isoindolin-2-yl)propyl)-2-(quinolin-8-yloxy)acetamide

HRID 1507042
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인쇄 미리보기

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HRID 1507042 반응식
[NH2:1][CH2:2][C@@H:3]([OH:14])[CH2:4][N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1.[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[O:25][CH2:26][C:27](OCC)=[O:28])[CH:18]=[CH:17][CH:16]=1>CCO>[OH:14][C@@H:3]([CH2:4][N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][NH:1][C:27](=[O:28])[CH2:26][O:25][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:24]=1[N:15]=[CH:16][CH:17]=[CH:18]2
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참가 물질

4

반응물 2

HCID 4379860Ethyl 2-(quinolin-8-yloxy)acetateHCID 86729441(R)-1-amino-3-(isoindolin-2-yl)propan-2-ol

생성물 1

HCID 76902226(R)-N-(2-hydroxy-3-(isoindolin-2-yl)propyl)-2-(quinolin-8-yloxy)acetamide수율 51%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
120 °C

실험 절차

(R)-1-amino-3-(isoindolin-2-yl)propan-2-ol (100 mg, 0.52 mmol) and ethyl 2-(quinolin-8-yloxy)acetate (120 mg, 0.52 mmol) were dissolved in EtOH (1 mL) and heated under microwave conditions at 120° C. for 0.5 h. The reaction mixture was concentrated and purified by preparative HPLC purification. (100 mg, yield 51%) MS (ESI+) e/z: 378.1 [M+1]+. 1H NMR (MeOD, 400 MHz), δ ppm: 8.95-8.85 (m, 1H), 8.44-8.34 (m, 1H), 7.69-7.54 (m, 3H), 7.33-7.27 (m, 1H), 7.18 (s, 4H), 4.79 (s, 2H), 4.09-4.03 (m, 1H), 3.99 (s, 4H), 3.61-3.53 (m, 1H), 3.47-3.38 (m, 1H), 2.91-2.85 (m, 1H), 2.84-2.77 (m, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by preparative HPLC purification

출처 및 근거

ORD 기록
ord-f00656ac657342168bca3d3a0881fa62
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221794B2

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