Potassium Carbonate → HCID 66929695, compound

HRID 1363325Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[O:8])[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:31][C:32]#[N:33]>CC(=O)CC>[NH2:1][C:2]1[N:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[O:8])[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:31][C:32]#[N:33])[CH:18]=2)[N:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

In particular, to a solution of 5-amino-3-[3-(hydroxy)phenylamino]-1-(2-(methyl)phenyl)carbonyl-1H-1,2,4-triazole (Ia-6) (0.23 g, 0.75 mmol) in 2-butanone (3 mL) was added K2CO3 (0.11 g, 0.83 mmol) and BrCH2CN (0.10 g, 0.83 mmol). After stirring the mixture at 75° C. for 20 h, the 2-butanone was removed under reduced pressure. The residue was dissolved in EtOAc (50 mL), washed with water (50 mL), brine (30 mL), dried (Na2SO4) and concentrated to afford the crude product. Purification by flash chromatography (1:1 hexanes/EtOAc) gave 5-amino-3-[3-(cyanomethoxy)phenylamino]-1-(2-(methyl)phenyl)carbonyl-1H-1,2,4-triazole (Ia-8) (0.09 g, 35%) as a white solid: Rf 0.29 (1:1 hexanes/ethyl acetate); mp (DSC) 204.5-207.9° C.;

Workup

customthe 2-butanone was removed under reduced pressure
dissolutionThe residue was dissolved in EtOAc (50 mL)
washwashed with water (50 mL), brine (30 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated
customto afford the crude product
customPurification by flash chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-bfb54f0f7bbe41a3b70ad66e7769b133
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884119B2

Reaction notes

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