2-Ethylcyclopentane-1,3-dione → (2S)-Ethyl-3-[4-(3-ethyl-isoquinolin-1-ylamino)phenyl]-2-[(2-ethyl-3-oxo-1-cyclopentenyl)amino]propionate

HRID 1837045

반응식

HRID 1837045 반응식
[CH2:1]([O:3][C:4](=[O:27])[C@@H:5]([NH2:26])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]([CH2:24][CH3:25])[N:15]=2)=[CH:9][CH:8]=1)[CH3:2].[CH2:28]([CH:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=O)[CH3:29]>ClCCCl>[CH2:1]([O:3][C:4](=[O:27])[C@@H:5]([NH:26][C:31]1[CH2:32][CH2:33][C:34](=[O:35])[C:30]=1[CH2:28][CH3:29])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]([CH2:24][CH3:25])[N:15]=2)=[CH:9][CH:8]=1)[CH3:2]

참가 물질

4

반응물 2

HCID 699782-Ethylcyclopentane-1,3-dioneHCID 69375403(S)-ethyl-3-[4-(3-ethyl-isoquinol-1-yl amino)phenyl]-2-aminopropionate

생성물 1

HCID 69377216(2S)-Ethyl-3-[4-(3-ethyl-isoquinolin-1-ylamino)phenyl]-2-[(2-ethyl-3-oxo-1-cyclopentenyl)amino]propionate수율 52.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A solution of (S)-ethyl-3-[4-(3-ethyl-isoquinol-1-yl amino)phenyl]-2-aminopropionate [prepared from 1-chloro,3-ethyl-isoquinoline (from reaction of o-toluic acid with propionitrile and subsequent treatment with phosphorous oxychloride) and N-BOC-L-4-aminophenylalanine ethylester] (750 mg, 2.07 mmol) and 2-ethyl-1,3-cyclopentanedione (273 mg, 2.17 mmol) in 1,2-dichloroethane (10 ml) was treated with 4 Å sieves (˜1 g) and heated at 90° for 3 days. The solution was filtered, concentrated in vacuo and the residue purified by chromatorgaphy (SiO2, 100:1 DCM/MeOH) to give the title compound as a brown solid (511 mg, 52%). δ H (d6-DMSO) 9.05 (1H, s), 8.46 (1H, d, J 7.0 Hz), 7.91 (2H, d, J 8.6 Hz), 7.72 (1H, d, J 7.0 Hz), 7.64 (1H, t, J 7.0 Hz), 7.51 (1H, t, J 7.0 Hz), 7.23 (2H, d, J 8.6 Hz), 6.99 (1H, s), 4.32 (1H, m), 4.15 (2H, q, J 7.1 Hz), 3.15 (1H, dd, J 13.5, 3.5 Hz), 3.01 (1H, dd, J 13.5, 9.6 Hz), 2.69 (2H, 1, J 7.5 Hz), 2.29 (1H, m), 2.18 (1H, m), 2.06 (4H, m), 1.28 (3H, t, J 7.5 Hz), 0.91 (3H, t, J 7.4 Hz). m/z (ESI, 70V) 472 (MH+).

후처리

  1. temperatureheated at 90° for 3 days
  2. filtrationThe solution was filtered
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by chromatorgaphy (SiO2, 100:1 DCM/MeOH)

출처 및 근거

ORD 기록
ord-193b757170c647659fb29b9ac19c539e
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06780874B2

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