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-methoxyquinolin-2-yl)methylidene]hydrazinyl]-3-pyridinyl]ethyl]pyrrolidin-3-yl]carbamate

HRID 338911Notes

Reaction equation

HRID 338911 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH:14]=O)[CH:6]=[CH:5]2.[F:16][C:17]([F:41])([F:40])[C@H:18]([N:27]1[CH2:31][CH2:30][C@H:29]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:28]1)[C:19]1[CH:20]=[N:21][C:22]([NH:25][NH2:26])=[CH:23][CH:24]=1>C(O)C>[F:40][C:17]([F:16])([F:41])[C@H:18]([N:27]1[CH2:31][CH2:30][C@H:29]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:38])[CH3:36])[CH2:28]1)[C:19]1[CH:20]=[N:21][C:22]([NH:25]/[N:26]=[CH:14]/[C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:2]([F:1])[CH:3]=3)[N:8]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 86707414tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateHCID 867074436-Fluoro-7-methoxyquinoline-2-carbaldehyde

Product 1

HCID 140629013tert-butyl N-[(3S)-1-[(1R)-2,2,2-trifluoro-1-[6-[(2E)-2-[(6-fluoro-7-methoxyquinolin-2-yl)methylidene]hydrazinyl]-3-pyridinyl]ethyl]pyrrolidin-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 6-fluoro-7-methoxyquinoline-2-carbaldehyde (54.7 mg, 0.266 mmol) in ethanol (5 mL) was added tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (100 mg, 0.266 mmol) and the reaction was stirred for 24 hours at ambient temperature. The reaction was concentrated to dryness and used as is in the next step.

Workup

  1. concentrationThe reaction was concentrated to dryness

Sources & evidence

ORD record
ord-d91909cb26f6410fabe1fbf5fcd54bbc
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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