tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate → tert-butyl N-[(3S)-1-[(1R)-2,2,2-trifluoro-1-[6-[(2E)-2-[(6-fluoro-8-propan-2-yloxyquinolin-2-yl)methylidene]hydrazinyl]-3-pyridinyl]ethyl]pyrrolidin-3-yl]carbamate

HRID 338888Notes

Reaction equation

HRID 338888 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][CH:39]([CH3:41])[CH3:40])[CH:37]=1)[N:34]=[C:33]([CH:42]=O)[CH:32]=[CH:31]2>C(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:5]=[N:6][C:7]([NH:10]/[N:11]=[CH:42]/[C:33]2[CH:32]=[CH:31][C:30]3[C:35](=[C:36]([O:38][CH:39]([CH3:41])[CH3:40])[CH:37]=[C:28]([F:27])[CH:29]=3)[N:34]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 86707414tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateHCID 867074316-Fluoro-8-isopropoxyquinoline-2-carbaldehyde

Product 1

HCID 140628990tert-butyl N-[(3S)-1-[(1R)-2,2,2-trifluoro-1-[6-[(2E)-2-[(6-fluoro-8-propan-2-yloxyquinolin-2-yl)methylidene]hydrazinyl]-3-pyridinyl]ethyl]pyrrolidin-3-yl]carbamateYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (100 mg, 0.266 mmol) and 6-fluoro-8-isopropoxyquinoline-2-carbaldehyde (62.1 mg, 0.266 mmol) were stirred in ethanol (5 mL) for 72 hours at ambient temperature. The reaction was concentrated under reduced pressure to yield tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-((E)-2-((6-fluoro-8-isopropoxyquinolin-2-yl)methylene)hydrazinyl)pyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (157 mg, 99.8% yield) as a yellow paste.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c9ccff82c4ab4b11a8ff5b2328210338
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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