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-(2-methoxyethoxy)-8-methylquinolin-2-yl]methylidene]hydrazinyl]pyridin-3-yl]ethyl]pyrrolidin-3-yl]carbamate

HRID 338924Notes

Reaction equation

HRID 338924 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][CH2:29][CH2:30][O:31][C:32]1[C:41]([CH3:42])=[C:40]2[C:35]([CH:36]=[CH:37][C:38]([CH:43]=O)=[N:39]2)=[CH:34][CH:33]=1>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:43]/[C:38]2[CH:37]=[CH:36][C:35]3[C:40](=[C:41]([CH3:42])[C:32]([O:31][CH2:30][CH2:29][O:28][CH3:27])=[CH:33][CH:34]=3)[N:39]=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 867074527-(2-Methoxyethoxy)-8-methylquinoline-2-carbaldehyde

Product 1

HCID 140628976tert-butyl N-[(3S)-1-[(1R)-2,2,2-trifluoro-1-[6-[(2E)-2-[[7-(2-methoxyethoxy)-8-methylquinolin-2-yl]methylidene]hydrazinyl]pyridin-3-yl]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 (98.0 mg, 0.261 mmol) and 7-(2-methoxyethoxy)-8-methylquinoline-2-carbaldehyde (64 mg, 0.261 mmol) were stirred in ethanol at ambient temperature for 24 hours. The reaction was concentrated and used as is in the next step.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-ac2e2b853a334949a094bddf3df37f07
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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