Triethylamine → 6-morpholin-4-yl-pyridine-3-sulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester

HRID 853672노트

반응식

HRID 853672 반응식
C(N(CC)CC)C.[N:8]1([C:14]2[N:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[CH:24]([O:37][C:38]1[C:39]2[C:51](=[O:52])[N:50]([CH2:53][C:54]3[CH:59]=[CH:58][C:57]([F:60])=[CH:56][CH:55]=3)[CH2:49][C:40]=2[C:41]([OH:48])=[C:42]2[C:47]=1[N:46]=[CH:45][CH:44]=[CH:43]2)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCOC(C)=O.CCCCCC>CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH:24]([O:37][C:38]1[C:39]2[C:51](=[O:52])[N:50]([CH2:53][C:54]3[CH:59]=[CH:58][C:57]([F:60])=[CH:56][CH:55]=3)[CH2:49][C:40]=2[C:41]([O:48][S:20]([C:17]2[CH:18]=[N:19][C:14]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)=[CH:15][CH:16]=2)(=[O:22])=[O:21])=[C:42]2[C:47]=1[N:46]=[CH:45][CH:44]=[CH:43]2)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 27764626-Morpholin-4-yl-pyridine-3-sulfonyl chlorideHCID 21226206Ethyl acetate hexaneHCID 1361585899-Benzhydryloxy-7-(4-fluoro-benzyl)-5-hydroxy-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one

생성물 1

HCID 589289306-morpholin-4-yl-pyridine-3-sulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester수율 59.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매

실험 절차

Triethylamine (50 μl), DMAP (catalytic amount) and 6-Morpholin-4-yl-pyridine-3-sulfonyl chloride (26.3 mg, 0.10 mmol) were added to 0.034 mmol 45. The reaction mixture was stirred at room temperature for 18 hours under an inert atmosphere. The reaction was monitored by TLC (EtOAc/hexane 3/7) (Rf 44=0.5, Rf 45=0, Rf 266=0.3) and LC/MS. After completion of the reaction, the mixture was diluted with EtOAc (20 mL) and washed with 1N HCl, saturated NaHCO3 and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethylacetate/hexane—3/7) to afford 6-morpholin-4-yl-pyridine-3-sulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester 266 (14.6 mg, 59%).

후처리

  1. customAfter completion of the reaction
  2. washwashed with 1N HCl, saturated NaHCO3 and brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (ethylacetate/hexane—3/7)

출처 및 근거

ORD 기록
ord-1d684a5d284245c09a08a2dec3171b66
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253180B2

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