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-7-propan-2-yloxyquinolin-2-yl)methylidene]hydrazinyl]-3-pyridinyl]ethyl]pyrrolidin-3-yl]carbamate

HRID 338932Notes

Reaction equation

HRID 338932 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](=[CH:36][C:37]=1[O:38][CH:39]([CH3:41])[CH3:40])[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](=[CH:36][C:37]([O:38][CH:39]([CH3:41])[CH3:40])=[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 867074576-Fluoro-7-isopropoxyquinoline-2-carbaldehyde

Product 1

HCID 140628985tert-butyl N-[(3S)-1-[(1R)-2,2,2-trifluoro-1-[6-[(2E)-2-[(6-fluoro-7-propan-2-yloxyquinolin-2-yl)methylidene]hydrazinyl]-3-pyridinyl]ethyl]pyrrolidin-3-yl]carbamate

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 (451 mg, 1.20 mmol) and 6-fluoro-7-isopropoxyquinoline-2-carbaldehyde (280 mg, 1.20 mmol) in ethanol (5 mL) were stirred at ambient temperature for 24 hours. After concentration, the residue was used in the next step without purification.

Workup

  1. concentrationAfter concentration
  2. customthe residue was used in the next step without purification

Sources & evidence

ORD record
ord-64dd500061344c54b10ece30f631342e
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…