Dichloromethane → 1-{3-[1-(2-Hydroxy-ethyl)-4-pyridin-4-yl-1H-pyrazol-3-yl]-phenyl}-3-(4-trifluoromethyl-phenyl)-urea

HRID 45817Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:21]3[CH:22]=[C:23]([NH:27][C:28]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=4)=[O:29])[CH:24]=[CH:25][CH:26]=3)=[N:9][N:10]([CH2:12][CH2:13][O:14]C3CCCCO3)[CH:11]=2)=[CH:3][CH:2]=1.C(Cl)Cl>>[OH:14][CH2:13][CH2:12][N:10]1[CH:11]=[C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[C:8]([C:21]2[CH:22]=[C:23]([NH:27][C:28]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:36]=3)=[O:29])[CH:24]=[CH:25][CH:26]=2)=[N:9]1

Participants

Reactant 2

HCID 6344Dichloromethane

HCID 67184338HCID 67184338, compound

Product 1

HCID 446228121-{3-[1-(2-Hydroxy-ethyl)-4-pyridin-4-yl-1H-pyrazol-3-yl]-phenyl}-3-(4-trifluoromethyl-phenyl)-urea

Procedure

To 1-(3-{4-pyridin-4-yl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-3-yl}-phenyl)-3-(4-trifluoromethyl-phenyl)-urea (50 mg, 0.09 mmol) in methylene chloride (1 mL) p-toluenesulfonic acid (PTSA) (25.8 mg, 0.13 mmol) was added, the reaction was stirred at room temperature for two days. The solvent was removed under reduced pressure and the product was isolated by silica gel column chromatography (DCM/methanol 93:7).

Workup

customThe solvent was removed under reduced pressure
customthe product was isolated by silica gel column chromatography (DCM/methanol 93:7)

Sources & evidence

ORD record: ord-74347965e4d74e1ead55d37fef4a3f7d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541575B2

Reaction notes

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