Iodo benzene diacetate → tert-butyl (S)-1-((S)-1-(3-(7-ethoxy-6-fluoro quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)-3-methylpyrrolidin-3-ylcarbamate

HRID 339035Notes

Reaction equation

HRID 339035 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@@:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:33])[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:42])[CH3:2].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>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@@:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:33])[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:42])[CH3:2]

Participants

4

Reactant 2

HCID 12217721Iodo benzene diacetateHCID 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]carbamate

Product 1

HCID 86707532tert-butyl (S)-1-((S)-1-(3-(7-ethoxy-6-fluoro quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)-3-methylpyrrolidin-3-ylcarbamateYield 85.83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (S)-1-((S)-1-(6-((E)-2-((7-ethoxy-6-fluoroquinolin-2-yl)methylene)hydrazinyl)pyridin-3-yl)-2,2,2-trifluoroethyl)-3-methylpyrrolidin-3-ylcarbamate (6.320 g, 10.70 mmol) and iodobenzene diacetate (3.447 g, 10.70 mmol) in DCM (50 mL) was stirred overnight at ambient temperature. The reaction was concentrated under reduced pressure and the residue subjected to chromatography (10% ethyl acetate/hexanes to 50% ethyl acetate/hexanes over 4 column volumes) to give tert-butyl (S)-1-((S)-1-(3-(7-ethoxy-6-fluoro quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)-3-methylpyrrolidin-3-ylcarbamate (5.406 g, 9.18 mmol, 85.83% yield).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-05f214913fe945649ee3297a75244159
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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