1-{3-[4-(2-aminopyrimidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazol-3-yl]phenyl}-3-[4-(trifluoromethyl)phenyl]urea → HCID 178508383, compound

HRID 45878Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:22]3[CH:23]=[C:24]([NH:28][C:29]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=4)=[O:30])[CH:25]=[CH:26][CH:27]=3)=[N:10][N:11](CC3C=CC(OC)=CC=3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1>FC(F)(F)C(O)=O>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:22]3[CH:23]=[C:24]([NH:28][C:29]([NH:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]([F:39])([F:40])[F:41])=[CH:34][CH:33]=4)=[O:30])[CH:25]=[CH:26][CH:27]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

800 mg (1.4 mmol) of 1-{3-[4-(2-aminopyrimidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazol-3-yl]phenyl}-3-[4-(trifluoromethyl)phenyl]urea were dissolved in 20 ml of trifluoroacetic acid and the mixture stirred at 70° C. for 4 hours. The solvent was then removed under reduced pressure and the residue taken up with dichloromethane and washed with aqueous sodium hydrogenocarbonate. The organic phase was dried over sodium sulphate and evaporated. The product was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3OH; from 99/1 to 95/5), giving 450 mg (73%) of the title compound.

Workup

customThe solvent was then removed under reduced pressure
washwashed with aqueous sodium hydrogenocarbonate
dry with materialThe organic phase was dried over sodium sulphate
customevaporated
customThe product was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3OH; from 99/1 to 95/5)

Sources & evidence

ORD record: ord-582a2b2f59804e768c7847e92ede356c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541575B2

Reaction notes

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