8-Isopropoxyquinoline-2-carbaldehyde → tert-butyl N-[(3S)-3-methyl-1-[(1S)-2,2,2-trifluoro-1-[6-[(2E)-2-[(8-propan-2-yloxyquinolin-2-yl)methylidene]hydrazinyl]-3-pyridinyl]ethyl]pyrrolidin-3-yl]carbamate

HRID 338893Notes

Reaction equation

HRID 338893 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.[CH:28]([O:31][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:41]=1[N:40]=[C:39]([CH:42]=O)[CH:38]=[CH:37]2)([CH3:30])[CH3:29]>C(O)C>[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:42]/[C:39]3[CH:38]=[CH:37][C:36]4[C:41](=[C:32]([O:31][CH:28]([CH3:30])[CH3:29])[CH:33]=[CH:34][CH:35]=4)[N:40]=3)=[CH:16][CH:17]=2)[C:8]([F:9])([F:10])[F:11])[CH2:3]1

Participants

4

Reactant 2

HCID 822418228-Isopropoxyquinoline-2-carbaldehydeHCID 86707435tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 140628986tert-butyl N-[(3S)-3-methyl-1-[(1S)-2,2,2-trifluoro-1-[6-[(2E)-2-[(8-propan-2-yloxyquinolin-2-yl)methylidene]hydrazinyl]-3-pyridinyl]ethyl]pyrrolidin-3-yl]carbamateYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 (1.30 g, 3.34 mmol) in Ethanol (25 mL) was added 8-isopropoxyquinoline-2-carbaldehyde (0.719 g, 3.34 mmol) and stirred at ambient temperature overnight. The reaction was concentrated 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-((8-isopropoxyquinolin-2-yl)methylene)hydrazinyl)pyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (1.33 g, 2.27 mmol, 67.9% yield).

Workup

  1. concentrationThe reaction was concentrated
  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-d3810e65ce3343e7bd9127decaa6e4da
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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