Acetic acid;iodosylbenzene → tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)-8-methylquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 338925Notes

Reaction equation

HRID 338925 reaction equation
[F:1][C:2]([F:43])([F:42])[C@H:3]([N:29]1[CH2:33][CH2:32][C@H:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:30]1)[C:4]1[CH:5]=[N:6][C:7]([NH:10]/[N:11]=[CH:12]/[C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([CH3:28])[C:17]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:18][CH:19]=3)[N:14]=2)=[CH:8][CH:9]=1.C(O)(=O)C.C(O)(=O)C.I(C1C=CC=CC=1)=O>C(Cl)Cl>[F:43][C:2]([F:42])([F:1])[C@H:3]([N:29]1[CH2:33][CH2:32][C@H:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:38])[CH3:39])[CH2:30]1)[C:4]1[CH:9]=[CH:8][C:7]2[N:6]([C:12]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[C:16]([CH3:28])[C:17]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:18][CH:19]=4)[N:14]=3)=[N:11][N:10]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 73357407Acetic acid;iodosylbenzeneHCID 140628976tert-butyl N-[(3S)-1-[(1R)-2,2,2-trifluoro-1-[6-[(2E)-2-[[7-(2-methoxyethoxy)-8-methylquinolin-2-yl]methylidene]hydrazinyl]pyridin-3-yl]ethyl]pyrrolidin-3-yl]carbamate

Product 1

HCID 86707454tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)-8-methylquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamateYield 59.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-((E)-2-((7-(2-methoxyethoxy)-8-methylquinolin-2-yl)methylene)hydrazinyl)pyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (157 mg, 0.261 mmol) in DCM (5 mL) was added iodosobenzene diacetate (101 mg, 0.313 mmol) and the reaction was stirred at ambient temperature for 2 hours. After concentration, the residue was purified by reverse phase chromatography (SP4, 12M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)-8-methylquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (93 mg, 59.4% yield) as a beige solid

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by reverse phase chromatography (SP4, 12M
  3. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-cd72ff3e9f0d4b44a59fae8944c37f47
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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