Iodo benzene diacetate → tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 338894Notes

Reaction equation

HRID 338894 reaction equation
[CH3:1][C@:2]1([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:13]=[N:14][C:15]([NH:18]/[N:19]=[CH:20]/[C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[C:24]([O:31][CH:32]([CH3:34])[CH3:33])[CH:25]=[CH:26][CH:27]=4)[N:22]=3)=[CH:16][CH:17]=2)[C:8]([F:11])([F:10])[F:9])[CH2:3]1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[CH3:1][C@:2]1([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:17]=[CH:16][C:15]3[N:14]([C:20]([C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[C:24]([O:31][CH:32]([CH3:34])[CH3:33])[CH:25]=[CH:26][CH:27]=5)[N:22]=4)=[N:19][N:18]=3)[CH:13]=2)[C:8]([F:11])([F:10])[F:9])[CH2:3]1

Participants

4

Reactant 2

HCID 12217721Iodo benzene diacetateHCID 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]carbamate

Product 1

HCID 86707436tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 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) in DCM (20 mL) was added iodo benzene diacetate (0.949 g, 2.95 mmol). The reaction mixture was stirred at ambient temperature for 2 hours and then partitioned between ethyl acetate and saturated aqueous NaHCO3. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by chromatography (1:3 hexane/ethyl acetate) to give tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(8-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (1.30 g, 98%).

Workup

  1. custompartitioned between ethyl acetate and saturated aqueous NaHCO3
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (1:3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1ff4b7c4e850493da15024f904e0d424
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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