N-(3-{4-[2-(ethylamino)pyrimidin-4-yl]-1-(4-methoxybenzyl)-1H-pyrazol-3-yl}phenyl)-2,5-difluorobenzenesulfonamide → HCID 178463412, compound

HRID 1843673Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([C:10]2[C:11]([C:24]3[CH:25]=[C:26]([NH:30][S:31]([C:34]4[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=4[F:41])(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=3)=[N:12][N:13](CC3C=CC(OC)=CC=3)[CH:14]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([C:10]2[C:11]([C:24]3[CH:25]=[C:26]([NH:30][S:31]([C:34]4[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=4[F:41])(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=3)=[N:12][NH:13][CH:14]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

450 mg (0.78 mmol) of N-(3-{4-[2-(ethylamino)pyrimidin-4-yl]-1-(4-methoxybenzyl)-1H-pyrazol-3-yl}phenyl)-2,5-difluorobenzenesulfonamide were dissolved in 10 ml of trifluoroacetic acid and the resulting solution heated at 70° C. under stirring for 4 hours. After this time the solvent was evaporated and the residue taken up with dichloromethane and washed with aqueous sodium hydrogenocarbonate. The organic phase was then dried over sodium sulphate and evaporated again. The crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3; from 9/1 to 8/2), giving 80 mg (22%) of the title compound.

Workup

customAfter this time the solvent was evaporated
washwashed with aqueous sodium hydrogenocarbonate
dry with materialThe organic phase was then dried over sodium sulphate
customevaporated again
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-c0b569d764cd42ad907074d693f1f752
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946250B2

Reaction notes

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