Water → HCID 135465356, compound

HRID 271444Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12](N3C=CN=C3)[N:11]3[C:19](=[O:22])[NH:20][N:21]=[C:10]3[C:9]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:37][C:38]1[CH:39]=[CH:40][C:41]([C:44]([F:47])([F:46])[F:45])=[N:42][CH:43]=1.[OH2:48]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:48])[N:11]3[C:19](=[O:22])[N:20]([CH2:37][C:38]4[CH:43]=[N:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=4)[N:21]=[C:10]3[C:9]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 7,8-bis(4-chlorophenyl)-5-(1H-imidazol-1-yl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (60 mg, 0.14 mmol) in DMF (0.5 mL) at room temperature under argon was added K2CO3 (25 mg, 0.18 mmol), followed by 5-(chloromethyl)-2-(trifluoromethyl)pyridine (28 mg, 0.14 mmol). The reaction mixture was stirred at 50° C. in a pre-heated oil bath for 30 min. After the reaction mixture was cooled to room temperature, water (5 mL) and EtOAc (5 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product thus obtained was purified by preparative reverse phase HPLC (without TFA) to obtain 22.5 mg of the title compound as a white solid. HPLC/MS: retention time=3.871 min, [M+H]30 =532.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customThe layers were separated
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product thus obtained
customwas purified by preparative reverse phase HPLC (without TFA)

Sources & evidence

ORD record: ord-7b61fecdf9674a12a63e8b0ee5144f80
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452892B2

Reaction notes

Loading…