tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate → tert-butyl N-[(3S)-3-methyl-1-[(1S)-2,2,2-trifluoro-1-[6-[(2E)-2-[(6-fluoro-8-methoxyquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]ethyl]pyrrolidin-3-yl]carbamate

HRID 339027Notes

Reaction equation

HRID 339027 reaction equation
[CH3:1][C@:2]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:13]=[N:14][C:15]([NH:18][NH2:19])=[CH:16][CH:17]=2)[C:8]([F:11])([F:10])[F:9])[CH2:3]1.[F:28][C:29]1[CH:30]=[C:31]2[C:36](=[C:37]([O:39][CH3:40])[CH:38]=1)[N:35]=[C:34]([CH:41]=O)[CH:33]=[CH:32]2>C(Cl)Cl>[CH3:1][C@:2]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:13]=[N:14][C:15]([NH:18]/[N:19]=[CH:41]/[C:34]3[CH:33]=[CH:32][C:31]4[C:36](=[C:37]([O:39][CH3:40])[CH:38]=[C:29]([F:28])[CH:30]=4)[N:35]=3)=[CH:16][CH:17]=2)[C:8]([F:9])([F:10])[F:11])[CH2:3]1

Participants

4

Reactant 2

HCID 86707435tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateHCID 867074476-Fluoro-8-methoxyquinoline-2-carbaldehyde

Product 1

HCID 140628987tert-butyl N-[(3S)-3-methyl-1-[(1S)-2,2,2-trifluoro-1-[6-[(2E)-2-[(6-fluoro-8-methoxyquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]ethyl]pyrrolidin-3-yl]carbamateYield 76.45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (1.00 g, 2.57 mmol) in DCM (15 mL) was added 6-fluoro-8-methoxyquinoline-2-carbaldehyde (0.5269 g, 2.568 mmol) and the reaction mixture was stirred at ambient temperature overnight. The reaction was concentrated under reduced pressure and the residue purified by chromatography (C18, 300 g, 10% MeCN/water to 95% MeCN/water over 25 column volumes) to give tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-((E)-2-((6-fluoro-8-methoxyquinolin-2-yl)methylene)hydrazinyl)pyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (1.132 g, 1.963 mmol, 76.45% yield).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue purified by chromatography (C18, 300 g, 10% MeCN/water to 95% MeCN/water over 25 column volumes)

Sources & evidence

ORD record
ord-529f83391d004af6ae98b51f3f0c9f73
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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