Triethylamine → N,N-dimethyl-3-(4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)pyridin-3-yl)prop-2-yn-1-amine

HRID 40264

Reaction equation

I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[N:14]2[N:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1.[CH3:25][N:26]([CH3:30])[CH2:27][C:28]#[CH:29].C(N(CC)CC)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:25][N:26]([CH3:30])[CH2:27][C:28]#[C:29][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[N:14]2[N:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (14.4 mg, 12.5 μmol) was added to a suspension of 3-((3-iodopyridin-4-yloxy)methyl)-6-phenyl-[1,2,4]triazolo[4,3-b]pyridazine (107 mg, 249 mmol) and 1-dimethylamino-2-propyne (80.4 μl, 748 μmol) in THF (0.6 mL) and triethylamine (591 μl, 4238 μmol) at RT. Copper(i) iodide, 99.999% (4.75 mg, 24.9 μmol) was added and the reaction mixture was stirred at 75° C. (oil bath) for ˜75 min. The reaction mixture was cooled at RT, concentrated in vacuo. Purification by MPLC (ISCO, CH2Cl2/MeOH: 100/0 to 90/10) afforded the title compound. MS m/z=385.1 [M+H]+. Calc'd for C22H20N6O: 384.44

Workup

temperatureThe reaction mixture was cooled at RT
concentrationconcentrated in vacuo
customPurification by MPLC (ISCO, CH2Cl2/MeOH: 100/0 to 90/10)

Sources & evidence

ORD record: ord-ecc27f9f768e4d41bcc7f7a720a62683
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524900B2

Linked notes

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