2-(Dimethylamino)ethanol → N,N-dimethyl-2-{[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]oxy}ethanamine

HRID 16004

Reaction equation

Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.C(N(CC)CC)C.[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][OH:33]>C(O)CCC>[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][O:33][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline, (100, 0.293), triethylamine (123 μL, 0.879 mmol), N,N-dimethylethanolamine (959 μL, 0.586 mmol) in n-butanol (3.0 mL) was heated in the microwave at 120° C. for 20 minutes, then concentrated. The crude product was purified by flash chromatography using a Horizon purification system on a 25S column eluting with chloroform/7 N ammonia in methanol (0.1-5%) to afford the title compound (75 mg, 74%).

Workup

concentrationconcentrated
customThe crude product was purified by flash chromatography
customa Horizon purification system on a 25S column
washeluting with chloroform/7 N ammonia in methanol (0.1-5%)

Sources & evidence

ORD record: ord-7e8a06e8dd3a4228b8636c042c325e3e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732604B2

Linked notes

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