Trifluoromethanesulfonic acid → HCID 117737018, compound

HRID 1504375Notes

Reaction equation

HRID 1504375 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:19]([N:22]([C:32]4[CH:36]=[CH:35][O:34][N:33]=4)CC4C=CC(OC)=CC=4)(=[O:21])=[O:20])=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:37])=[C:4]([O:38][CH2:39][C:40]#[N:41])[CH:3]=1.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:19]([NH:22][C:32]4[CH:36]=[CH:35][O:34][N:33]=4)(=[O:20])=[O:21])=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:37])=[C:4]([O:38][CH2:39][C:40]#[N:41])[CH:3]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 117737146HCID 117737146, compound

Product 1

HCID 117737018HCID 117737018, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-bromo-2-(cyanomethoxy)-5-fluorophenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.80 g, 1.251 mmol) in DCM (12.51 ml) at room temperature was added trifluoromethanesulfonic acid (0.333 ml, 3.75 mmol). The resulting solution was stirred for 20 minutes and LCMS indicated that the reaction was complete. The reaction mixture was concentrated and loaded directly onto an silica column and purified by ISCO MPLC (100% heptanes to 75% 3:1 EtOAc:EtOH). The product eluted at 75% 3:1 EtOAc:EtOH. m/z (ESI) 522.9 (M+1)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by ISCO MPLC (100% heptanes to 75% 3:1 EtOAc:EtOH)
  3. washThe product eluted at 75% 3:1 EtOAc

Sources & evidence

ORD record
ord-ee80790b697a4d0493f1df4311fa7f49
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

Loading…