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-[(7-methoxy-6-methylquinolin-2-yl)methylidene]hydrazinyl]-3-pyridinyl]ethyl]pyrrolidin-3-yl]carbamate

HRID 338952Notes

Reaction equation

HRID 338952 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.[CH3:27][O:28][C:29]1[CH:38]=[C:37]2[C:32]([CH:33]=[CH:34][C:35]([CH:39]=O)=[N:36]2)=[CH:31][C:30]=1[CH3:41]>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:39]/[C:35]2[CH:34]=[CH:33][C:32]3[C:37](=[CH:38][C:29]([O:28][CH3:27])=[C:30]([CH3:41])[CH:31]=3)[N:36]=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 867074727-Methoxy-6-methylquinoline-2-carbaldehyde

Product 1

HCID 140629011tert-butyl N-[(3S)-1-[(1R)-2,2,2-trifluoro-1-[6-[(2E)-2-[(7-methoxy-6-methylquinolin-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 (187 mg, 0.497 mmol) and 7-methoxy-6-methylquinoline-2-carbaldehyde (100 mg, 0.497 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-cbb0cbbf5ebf4a71816e614ea14f36d6
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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