Dimethylamine → N-(3-(4-(4-chlorobenzyl)-6-(dimethylamino)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide

HRID 1624878Notes

Reaction equation

[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11](Br)=[N:10][N:9]([C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:18]=[CH:19][CH:20]=3)[C:8]2=[O:25])=[CH:4][CH:3]=1.[CH3:28][NH:29][CH3:30].CO>CN(C=O)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([N:29]([CH3:30])[CH3:28])=[N:10][N:9]([C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:24])[CH3:23])[CH:18]=[CH:19][CH:20]=3)[C:8]2=[O:25])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

According to Scheme 2 Step 4: To a solution of 2(C) (100 mg, 0.22 mmol) in 0.5 mL of DMF was added dimethylamine 2M solution in methanol (0.56 mL, 1.11 mmol). The reaction was heated 5 h at 150° C. under microwave irradiation. The reaction mixture was quenched with water and extracted with ethyl acetate (×3). The combined organic layers were washed successively with water, with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography, 5 g column (Eluant: DCM/MeOH 98/2). 10 mg, (11% yield) of N-(3-(4-(4-chlorobenzyl)-6-(dimethylamino)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 2(D) were obtained.

Workup

customThe reaction mixture was quenched with water
extractionextracted with ethyl acetate (×3)
washThe combined organic layers were washed successively with water, with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash chromatography, 5 g column (Eluant: DCM/MeOH 98/2)

Sources & evidence

ORD record: ord-e2db5cf70e184b15a292460916d64751
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779129B2

Reaction notes

Loading…