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

HRID 45886Notes

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-fa5024f212ab44cfbbc43a7090a052c9
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541575B2

Reaction notes

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