HCID 117737203, compound → HCID 117737243, compound

HRID 1504504Notes

Reaction equation

HRID 1504504 reaction equation
[F:1][C:2]1[C:3]([N:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][C:40]2=[O:46])=[CH:4][C:5]([O:37][CH3:38])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([N:21]([C:31]4[CH:35]=[CH:34][O:33][N:32]=4)CC4C=CC(OC)=CC=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:36])[CH:7]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[C:3]([N:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][C:40]2=[O:46])=[CH:4][C:5]([O:37][CH3:38])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH:21][C:31]4[CH:35]=[CH:34][O:33][N:32]=4)(=[O:19])=[O:20])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]2=[O:36])[CH:7]=1

Participants

3

Reactant 1

HCID 117737203HCID 117737203, compound

Product 1

HCID 117737243HCID 117737243, compoundYield 1.64%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-(5-Fluoro-2-methoxy-4-(4-methyl-2-oxopyridin-1(2H)-yl)phenyl)-N-(isoxazol-3-yl)-N-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (18 mg, 0.028 mmol) was taken up in TFA (2 mL) in a microwave vial and irradiated to 70° C. for 1 h. Concentration under a stream of N2 followed by column chromatography (5 g Redisep gold column, 0-80% [3:1 EtOAc/EtOH]/hept gradient with 10% DCM) afforded 1-(5-fluoro-2-methoxy-4-(4-methyl-2-oxo-1(2H)-pyridinyl)phenyl)-N-3-isoxazolyl-2-oxo-1,2-dihydro-6-quinolinesulfonamide (0.24 mg, 0.459 μmol, 1.640% yield) as a colorless residue. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.55 (s, 3 H) 3.72 (s, 3 H) 6.64 (d, J=1.76 Hz, 1 H) 6.88 (d, J=9.74 Hz, 1 H) 6.98-7.02 (m, 2 H) 7.11 (d, J=6.84 Hz, 1 H) 7.32 (d, J=1.35 Hz, 2H) 7.80-7.90 (m, 2 H) 8.15 (d, J=2.07 Hz, 1 H) 8.23 (d, J=5.39 Hz, 1 H) 8.29 (d, J=1.66 Hz, 1 H). m/z (ESI) 523.0 (M+H)+.

Workup

  1. customirradiated to 70° C. for 1 h
  2. concentrationConcentration under a stream of N2

Sources & evidence

ORD record
ord-17e24f84017640d3867ccca73b99c3ff
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

Loading…