4-Chloro-7-methoxycinnoline → HCID 68617576, 화합물

HRID 2405817노트

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HRID 2405817 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:10]([N:12]1[CH2:16][CH:15]([OH:17])[CH2:14][CH:13]1[C:18]([NH:20][C:21]1([C:26]([OH:28])=[O:27])[CH2:23][CH:22]1[CH2:24][CH3:25])=[O:19])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[K+].Cl[C:40]1[C:49]2[C:44](=[CH:45][C:46]([O:50][CH3:51])=[CH:47][CH:48]=2)[N:43]=[N:42][CH:41]=1>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:29]([CH3:31])([CH3:30])[CH3:32])[C:10]([N:12]1[CH2:16][CH:15]([O:17][C:40]2[C:49]3[C:44](=[CH:45][C:46]([O:50][CH3:51])=[CH:47][CH:48]=3)[N:43]=[N:42][CH:41]=2)[CH2:14][CH:13]1[C:18]([NH:20][C:21]1([C:26]([OH:28])=[O:27])[CH2:23][CH:22]1[CH2:24][CH3:25])=[O:19])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 219910214-Chloro-7-methoxycinnolineHCID 23665647Potassium tert-butoxideHCID 686163761-{[1-(2-tert-Butoxycarbonylamino-3,3-dimethylbutyryl)-4-hydroxypyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid

생성물 1

HCID 68617576HCID 68617576, 화합물수율 57%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To 1-{[1-(2-tert-butoxycarbonylamino-3,3-dimethyl-butyryl)-4-hydroxy-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid (210 mmg, 0.46 mmol) at 0° C. (external temperature, ice bath) was added KOt-Bu (1 m in THF, 2.3 mL, 2.3 mmol, 5 equiv.) and 4-chloro-7-methoxy-cinnoline (95 mg, 0.49 mmol, 1.06 equiv.) in THF (3 mL). The reaction was stirred at 0° C. for 2.5 h and diluted with EtOAc. The solution was washed with aqueous HCl (1M), resulting a precipitation of the crude product. The organic layer was dried over Na2SO4 and combined with the precipitate. The crude product was purified by column chromatography (0→15% MeOH/CH2Cl2) to provide 1-{[1-(2-tert-butoxycarbonylamino-3,3-dimethyl-butyryl)-4-(7-methoxy-cinnolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid (161 mg, 57%).

후처리

  1. washThe solution was washed with aqueous HCl (1M)
  2. customresulting
  3. customa precipitation of the crude product
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customThe crude product was purified by column chromatography (0→15% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-60b4571f04414d34b4ce55f17e1f892c
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809267B2

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