2,5-difluoro-N-(3-{1-(4-methoxybenzyl)-4-[2-(methylamino)-pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)benzenesulfonamide → HCID 178482072, compound

HRID 1843656Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH3:31])[CH:25]=3)=[CH:22][N:21](CC3C=CC(OC)=CC=3)[N:20]=2)[CH:14]=1)(=[O:11])=[O:10]>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH3:31])[CH:25]=3)=[CH:22][NH:21][N:20]=2)[CH:14]=1)(=[O:10])=[O:11]

Participants

Conditions

Temperature: 70 °C

Procedure

300 mg (0.53 mmol) of 2,5-difluoro-N-(3-{1-(4-methoxybenzyl)-4-[2-(methylamino)-pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)benzenesulfonamide were dissolved in 10 ml of trifluoroacetic acid and the mixture heated at 70° C. under stirring for 4 hours. The solvent was then removed in vacuo, the residue partitioned between dichloromethane and a saturated aqueous solution of sodium hydrogenocarbonate. The organic layer was dried over sodium sulphate and evaporated to dryness. The crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 8/2), giving 47 mg (20%) of the title compound.

Workup

customThe solvent was then removed in vacuo
customthe residue partitioned between dichloromethane
dry with materialThe organic layer was dried over sodium sulphate
customevaporated to dryness
customThe crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 8/2)

Sources & evidence

ORD record: ord-9a0a3f533b494937bd900d918e83fdff
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946250B2

Reaction notes

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