Ethanol → tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(8-((R)-1-methoxypropan-2-yloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 338957노트

반응식

HRID 338957 반응식
[F:1][C:2]([F:26])([F:25])[C@H:3]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13]1)[C:4]1[CH:5]=[N:6][C:7]([NH:10][NH2:11])=[CH:8][CH:9]=1.[CH3:27][O:28][CH2:29][C@H:30]([O:32][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:42]=1[N:41]=[C:40]([CH:43]=O)[CH:39]=[CH:38]2)[CH3:31].C(O)C.C(O)(=O)C.C(O)(=O)C.I(C1C=CC=CC=1)=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[F:26][C:2]([F:25])([F:1])[C@H:3]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])[CH2:13]1)[C:4]1[CH:9]=[CH:8][C:7]2[N:6]([C:43]([C:40]3[CH:39]=[CH:38][C:37]4[C:42](=[C:33]([O:32][C@H:30]([CH3:31])[CH2:29][O:28][CH3:27])[CH:34]=[CH:35][CH:36]=4)[N:41]=3)=[N:11][N:10]=2)[CH:5]=1

참가 물질

7

반응물 5

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 73357407Acetic acid;iodosylbenzeneHCID 86707414tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateHCID 86707475(R)-8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehyde

생성물 1

HCID 86707476tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(8-((R)-1-methoxypropan-2-yloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate수율 73%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A solution of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (0.33 g, 0.87 mmol) and (R)-8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehyde (0.21 g, 0.87 mmol) in ethanol (4.3 mL, 0.87 mmol) was allowed to stir at ambient temperature for 12 hours. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (4.3 mL) and iodosobenzene diacetate (0.31 g, 0.95 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 hour. Ethyl acetate (20 mL) and saturated sodium bicarbonate (10 mL) were added. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography on C18 (25-100% acetonitrile/water) to give the title compound (0.38 g, 73%).

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (4.3 mL)
  3. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by reverse phase chromatography on C18 (25-100% acetonitrile/water)

출처 및 근거

ORD 기록
ord-661e2350a71e41d3873925c15a000256
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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