tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate → tert-butyl N-[(3S)-1-[(1S)-1-[6-[(2E)-2-[(7-ethoxy-6-fluoroquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]-2,2,2-trifluoroethyl]-3-methylpyrrolidin-3-yl]carbamate

HRID 339034Notes

Reaction equation

HRID 339034 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.[CH2:28]([O:30][C:31]1[CH:40]=[C:39]2[C:34]([CH:35]=[CH:36][C:37]([CH:41]=O)=[N:38]2)=[CH:33][C:32]=1[F:43])[CH3:29]>C(O)C>[CH2:28]([O:30][C:31]1[CH:40]=[C:39]2[C:34]([CH:35]=[CH:36][C:37](/[CH:41]=[N:19]/[NH:18][C:15]3[N:14]=[CH:13][C:12]([C@H:7]([N:4]4[CH2:5][CH2:6][C@@:2]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:1])[CH2:3]4)[C:8]([F:9])([F:10])[F:11])=[CH:17][CH:16]=3)=[N:38]2)=[CH:33][C:32]=1[F:43])[CH3:29]

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 867074687-Ethoxy-6-fluoroquinoline-2-carbaldehyde

Product 1

HCID 140628978tert-butyl N-[(3S)-1-[(1S)-1-[6-[(2E)-2-[(7-ethoxy-6-fluoroquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]-2,2,2-trifluoroethyl]-3-methylpyrrolidin-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 (Example 122, Steps A and B; 5.113 g, 13.13 mmol) in ethanol (25 mL) was added 7-ethoxy-6-fluoroquinoline-2-carbaldehyde (2.878 g, 13.13 mmol) and stirred overnight at ambient temperature. The precipitate was filtered to give desired product as a pale yellow solid (5.276 g). The filtrate was subjected to chromatography (C18, 300 g, 75 mL/min, 10% MeCN/H2O to 95% MeCN over 25 column volumes) and combined with the filtered product to give tert-butyl (S)-1-((S)-1-(6-((E)-2-((7-ethoxy-6-fluoro quinolin-2-yl)methylene)hydrazinyl)pyridin-3-yl)-2,2,2-trifluoroethyl)-3-methylpyrrolidin-3-ylcarbamate (6.322 g, 10.70 mmol, 81.53% yield).

Workup

  1. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-30521f75b2194b45b0f55576cc8fee95
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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