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

HRID 338984
Notes
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Reaction equation

HRID 338984 reaction equation
[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.[F:27][C:28]1[CH:29]=[C:30]2[C:35](=[C:36]([O:38][C@H:39]([CH3:43])[CH2:40][O:41][CH3:42])[CH:37]=1)[N:34]=[C:33]([CH:44]=O)[CH:32]=[CH:31]2.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:44]([C:33]3[CH:32]=[CH:31][C:30]4[C:35](=[C:36]([O:38][C@H:39]([CH3:43])[CH2:40][O:41][CH3:42])[CH:37]=[C:28]([F:27])[CH:29]=4)[N:34]=3)=[N:11][N:10]=2)[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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 86707493(R)-6-fluoro-8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehyde

Product 1

HCID 86707494
tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-8-((R)-1-methoxypropan-2-yloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate
Yield 45.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (0.16 g, 0.43 mmol) and (R)-6-fluoro-8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehyde (0.11 g, 0.43 mmol) in ethanol (2.2 mL, 0.43 mmol) was allowed to stir at ambient temperature for 12 hours. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (2.2 mL) and iodosobenzene diacetate (0.15 g, 0.47 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 (0-100% acetonitrile/water) to give the title compound (0.12 g, 44%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (2.2 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 (0-100% acetonitrile/water)

Sources & evidence

ORD record
ord-a637dbf9914c4a3b8e647f619dcd17cc
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889704B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes