Tetrahydrofuran → Benzyl [2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(1-hydroxy-1-methylethyl)quinolin-3-yl]carbamate

HRID 924392노트

반응식

HRID 924392 반응식
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH:37][C:38]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:39])[C:10]([C:14]([NH:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:22]=3[N:23]3[CH2:28][CH2:27][CH2:26][C@H:25]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24]3)=[O:15])=[N:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:48]1COCC1>C[Mg]Br.CCOC(C)=O.Cl>[C:32]([O:31][C:30]([NH:29][C@H:25]1[CH2:26][CH2:27][CH2:28][N:23]([C:22]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[NH:16][C:14]([C:10]2[C:9]([NH:37][C:38](=[O:39])[O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[CH:8][C:7]3[C:12](=[CH:13][C:4]([C:1]([OH:3])([CH3:48])[CH3:2])=[CH:5][CH:6]=3)[N:11]=2)=[O:15])[CH2:24]1)=[O:36])([CH3:35])([CH3:34])[CH3:33]

참가 물질

6

반응물 2

HCID 8028Tetrahydrofuran2회HCID 86726872tert-Butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate

생성물 1

HCID 90287190Benzyl [2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(1-hydroxy-1-methylethyl)quinolin-3-yl]carbamate수율 92%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 8857Ethyl Acetate용매HCID 178418573HCID 178418573, 화합물용매

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온도
0 °C

실험 절차

To a mixture of tert-butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate (0.100 g, 0.156 mmol) in THF (4.0 mL), methylmagnesium bromide in THF (3.0 M, 0.43 mL, 1.3 mmol) was added slowly at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 1 h and was then allowed to warm to room temperature. The reaction mixture was diluted with EtOAc (10 mL), and 1 M HCl was slowly added to adjust the pH to 7. The aqueous layer was extracted twice with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered and concentrated under reduced pressure to give the sub-title compound (94 mg, 92%). LCMS calc. for C36H43N6O6 (M+H)+: m/z=655.2. Found: 655.1.

후처리

  1. additionwas added slowly at 0° C. under nitrogen
  2. temperatureto warm to room temperature
  3. additionwas slowly added
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-10920f94531d42d695822b70e8391cc9
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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