Water → 2-{4-Methoxy-2-[(3-{[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}quinoxalin-2-yl)amino]phenyl}ethyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate

HRID 1914727노트

반응식

HRID 1914727 반응식
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[NH:12][C:13]1[C:14]([NH:23][S:24]([C:27]2[N:28]=[CH:29][N:30]([CH3:32])[CH:31]=2)(=[O:26])=[O:25])=[N:15][C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2.Cl.CN(C)CCCN=C=NCC.[C:45]([NH:62][C@H:63]([C:67](O)=[O:68])[CH:64]([CH3:66])[CH3:65])([O:47][CH2:48][CH:49]1[C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[C:55]2[C:50]1=[CH:51][CH:52]=[CH:53][CH:54]=2)=[O:46].O>CN(C)C1C=CN=CC=1.C(Cl)Cl.CN(C=O)C>[CH:51]1[C:50]2[CH:49]([CH2:48][O:47][C:45]([NH:62][C@H:63]([C:67]([O:1][CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=3[NH:12][C:13]3[C:14]([NH:23][S:24]([C:27]4[N:28]=[CH:29][N:30]([CH3:32])[CH:31]=4)(=[O:26])=[O:25])=[N:15][C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:22]=3)=[O:68])[CH:64]([CH3:65])[CH3:66])=[O:46])[C:61]3[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=3)[C:55]=2[CH:54]=[CH:53][CH:52]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 688217FMOC-L-valineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 24992804N-(3-{[2-(2-hydroxyethyl)-5-methoxyphenyl]amino}quinoxalin-2-yl)-1-methyl-1H-imidazole-4-sulfonamide

생성물 1

HCID 249953232-{4-Methoxy-2-[(3-{[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}quinoxalin-2-yl)amino]phenyl}ethyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate수율 59%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a suspension of N-(3-{[2-(2-hydroxyethyl)-5-methoxyphenyl]amino}quinoxalin-2-yl)-1-methyl-1H-imidazole-4-sulfonamide (200 mg; 0.44 mmol; 1 eq), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (92.8 mg; 0.48 mmol; 1.1 eq) and N,N-dimethylpyridin-4-amine (59 mg; 0.48 mmol; 1.1 eq) in a mixture of DCM (10 mL) and DMF (1 mL) is added fmoc-l-valine (164 mg; 0.48 mmol; 1.1 eq). The reaction mixture is stirred for 18 h at room temperature. Water is added and organic phase is washed several times with 10% citric acid then dried under MgSO4. The solvent is removed under reduced pressure and residue purified by flash chromatography using EtOAc as eluent to afford 200 mg (59%) of the title compound as a yellow gum. HPLC (max plot) 98%; Rt 5.46 min. LC/MS: (ES+): 775.7, (ES−): 773.9.

후처리

  1. washorganic phase is washed several times with 10% citric acid
  2. customthen dried under MgSO4
  3. customThe solvent is removed under reduced pressure and residue
  4. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-a6b18c522c5f4cdcb7d040f5c37c6c51
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614215B2

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