Sodium Bicarbonate → tert-butyl (3S)-1-(2,2,2-trifluoro-1-(3-(8-methoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 338837노트

반응식

HRID 338837 반응식
[F:1][C:2]([F:26])([F:25])[CH: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][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]2[C:38]=1[N:37]=[C:36]([CH:39]=O)[CH:35]=[CH:34]2.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CCO.C(OCC)(=O)C>[F:26][C:2]([F:25])([F:1])[CH: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:39]([C:36]3[CH:35]=[CH:34][C:33]4[C:38](=[C:29]([O:28][CH3:27])[CH:30]=[CH:31][CH:32]=4)[N:37]=3)=[N:11][N:10]=2)[CH:5]=1

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 15488708-Methoxyquinoline-2-carbaldehydeHCID 12217721Iodo benzene diacetateHCID 86707403tert-butyl (3S)-1-(2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate

생성물 1

HCID 86707404tert-butyl (3S)-1-(2,2,2-trifluoro-1-(3-(8-methoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate수율 93.9%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of tert-butyl (3S)-1-(2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (0.20 g, 0.53 mmol) and 8-methoxyquinoline-2-carbaldehyde (0.105 g, 0.53 mmol) in EtOH (10 mL) was stirred at ambient temperature for 1 hour. The solvent was removed under reduced pressure. The residue was dissolved in DCM (10 mL) and iodobenzene diacetate (0.189 g, 0.59 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 (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluting with ethyl acetate) to give tert-butyl (3S)-1-(2,2,2-trifluoro-1-(3-(8-methoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.27 g, 93.4%) as off white solid.

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in DCM (10 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (eluting with ethyl acetate)

출처 및 근거

ORD 기록
ord-4f28b7712698486991b2c43700c0edf2
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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