Trifluoroacetic acid → cyclopentyl-3-((3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl)ethynyl)azetidine-1-carboxylate

HRID 1188264Notes

Reaction equation

HRID 1188264 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]#[C:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:28])[C:12]([C:17]4[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=4)=[CH:13][O:14]3)=[CH:9][CH:8]=2)[CH2:2]1.FC(F)(F)C(O)=O.[C:36](=O)([O:43]N1C(=O)CCC1=O)[O:37][CH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1.C(N(C(C)C)CC)(C)C>ClCCl>[CH:38]1([O:37][C:36]([N:1]2[CH2:4][CH:3]([C:5]#[C:6][C:7]3[CH:16]=[C:15]4[C:10]([C:11](=[O:28])[C:12]([C:17]5[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=5)=[CH:13][O:14]4)=[CH:9][CH:8]=3)[CH2:2]2)=[O:43])[CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 15927743N-(Cyclopentyloxycarbonyloxy)succinimideHCID 71506445N-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

Product 1

HCID 71506446cyclopentyl-3-((3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl)ethynyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(4-(7-(azetidin-3-ylethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide.trifluoroacetic acid salt (55 mgs, 0.140 mmol) in dichloromethane (3 mL) was added cyclopentyl 2,5-dioxopyrrolidin-1-yl carbonate (95 mgs, 0.42 mmol) and diisopropylethylamine (0.2 mL, 1.4 mmol), and the mixture was stirred at room temperature for 16 hours. The resulting mixture was concentrated under reduced pressure, and chromatographed (SiO2, 25% ethyl acetate/dichloromethane) to provide cyclopentyl-3-((3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl)ethynyl)azetidine-1-carboxylate:

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customchromatographed (SiO2, 25% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-227737d604f043dea950a514f9124930
Source dataset
uspto-grants-2014_03
Patent number
US08673966B2

Reaction notes

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