Water → HCID 86686816, compound

HRID 1403169Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[N:23]=[C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:21]=[C:20]([N:30]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[N:32]=[C:31]2[CH:39]([F:41])[F:40])[N:19]=1.O>CN(C)C=O.C(Cl)(Cl)Cl>[F:41][CH:39]([F:40])[C:31]1[N:30]([C:20]2[N:21]=[C:22]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[N:23]=[C:18]([O:1][C:2]3[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=3)[N:19]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(4-hydroxyphenyl)ethanone (5.4 mg) in N,N-dimethylformamide (200 μL) were added potassium carbonate (6.9 mg) and a solution of 1-[4-chloro-6-(morpholin-4-yl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole (9.2 mg) in N,N-dimethylformamide (300 μL), followed by stirring at 80° C. overnight. To the reaction solution were added water and chloroform at room temperature, followed by liquid-liquid phase separation, and the organic layer was evaporated under reduced pressure. The residue was purified by preparative HPLC to obtain 1-[4-({4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)-1,3,5-triazin-2-yl}oxy)phenyl]ethanone (1.4 mg).

Workup

customfollowed by liquid-liquid phase separation
customthe organic layer was evaporated under reduced pressure
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-b23de7ac44b54e6ea9730c33dfe1901a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912180B2

Reaction notes

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