Iodosobenzene acetate → tert-butyl (S)-1-((R)-1-(3-(7-ethoxy-6-fluoroquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate

HRID 338948Notes

Reaction equation

HRID 338948 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10](/[CH:14]=[N:15]/[NH:16][C:17]3[N:22]=[CH:21][C:20]([C@@H:23]([N:28]4[CH2:32][CH2:31][C@H:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:29]4)[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)=[N:11]2)=[CH:6][C:5]=1[F:41])[CH3:2].C(O)(=O)C.I(C1C=CC=CC=1)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([C:14]3[N:22]4[CH:21]=[C:20]([C@@H:23]([N:28]5[CH2:32][CH2:31][C@H:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:37])([CH3:39])[CH3:38])[CH2:29]5)[C:24]([F:27])([F:25])[F:26])[CH:19]=[CH:18][C:17]4=[N:16][N:15]=3)=[N:11]2)=[CH:6][C:5]=1[F:41])[CH3:2]

Participants

4

Reactant 2

HCID 18539650Iodosobenzene acetateHCID 140628984tert-butyl N-[(3S)-1-[(1R)-1-[6-[(2E)-2-[(7-ethoxy-6-fluoroquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]-2,2,2-trifluoroethyl]pyrrolidin-3-yl]carbamate

Product 1

HCID 86707470tert-butyl (S)-1-((R)-1-(3-(7-ethoxy-6-fluoroquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamateYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl (S)-1-((R)-1-(6-((E)-2-((7-ethoxy-6-fluoro quinolin-2-yl)methylene)hydrazinyl)pyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (368 mg, 0.638 mmol) in DCM was added iodosobenzene acetate (267 mg, 0.830 mmol) and the reaction was stirred at ambient temperature for 2 hours. After concentration, the residue was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield tert-butyl (S)-1-((R)-1-(3-(7-ethoxy-6-fluoroquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (265 mg, 72.3% yield) as a beige solid

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by reverse phase chromatography (SP4, 25M
  3. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-71a5604c25f1454cab54f83d903627ad
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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