(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride → 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)urea

HRID 1842915Notes

Reaction equation

[OH:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:21])OC3C=CC=CC=3)=[CH:8][CH:7]=2)[CH2:5][O:4][CH2:3]1.Cl.[Cl:23][C:24]1[CH:25]=[C:26]([N:30]2[C:34]([CH2:35][NH2:36])=[CH:33][C:32]([C:37]([F:40])([F:39])[F:38])=[N:31]2)[CH:27]=[CH:28][CH:29]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:25]=[C:26]([N:30]2[C:34]([CH2:35][NH:36][C:13]([NH:12][C:9]3[CH:8]=[CH:7][C:6]([C:2]4([OH:1])[CH2:3][O:4][CH2:5]4)=[CH:11][CH:10]=3)=[O:21])=[CH:33][C:32]([C:37]([F:38])([F:39])[F:40])=[N:31]2)[CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of phenyl 4-(3-hydroxyoxetan-3-yl)phenylcarbamate (100 mg, 0.35 mmol, 1.0 eq) and (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (119.3 mg, 0.35 mmol, 1.0 eq) in DCM (10 mL) was added TEA (106 mg, 1.049 mmol, 3.0 eq) at RT and stirred at 40° C. overnight. The mixture was diluted with DCM (30 mL) and washed with water (10 mL), brine (10 mL) and dried over anhydrous Na2SO4 and concentrated. Crude product was purified by CC using MeOH/CHCl3 (1:9) to get 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)urea (100 mg; 61%) as a white solid (TLC system: MeOH/CHCl3 (1:9); Rf: 0.45).

Workup

washwashed with water (10 mL), brine (10 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customCrude product was purified by CC

Sources & evidence

ORD record: ord-63c6e07def374b28a22cb2f2aad6ed57
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946204B2

Reaction notes

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