Triethylamine → 7-methoxy-N-((6-(2-(triethylsilyl)ethynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-1,5-naphthyridin-4-amine

HRID 40202Notes

Reaction equation

HRID 40202 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][NH:12][C:13]3[C:22]4[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][N:21]=4)[N:16]=[CH:15][CH:14]=3)=[N:9][N:10]=2)[N:7]=1.[CH2:25]([Si:27]([CH2:32][CH3:33])([CH2:30][CH3:31])[C:28]#[CH:29])[CH3:26].C(N(CC)CC)C>C(#N)C.[Cu]I>[CH3:24][O:23][C:19]1[CH:18]=[C:17]2[C:22]([C:13]([NH:12][CH2:11][C:8]3[N:6]4[N:7]=[C:2]([C:26]#[C:25][Si:27]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH2:28][CH3:29])[CH:3]=[CH:4][C:5]4=[N:10][N:9]=3)=[CH:14][CH:15]=[N:16]2)=[N:21][CH:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 637947(Triethylsilyl)acetyleneHCID 44180710N-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine

Product 1

HCID 576909307-methoxy-N-((6-(2-(triethylsilyl)ethynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-1,5-naphthyridin-4-amine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

To an argon flushed pressure vial (15 mL) was added copper (I)iodide (0.0070 g, 0.037 mmol), PdCl2(dppf)-CH2Cl2Adduct (0.012 g, 0.015 mmol), N-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine (0.050 g, 0.15 mmol), and triethyl(ethynyl)silane (0.13 ml, 0.73 mmol) in acetonitrile (2 mL) followed by triethylamine (0.61 ml, 4.4 mmol). The vial was sealed and stirred at room temperature overnight The solution was concentrated and purified by MPLC (eluted with 0-10% (90:10:1 DCM:MeOH:NH4OH)) to yield the product as a light yellow solid. MS m/z=446.1 [M+1]+. Calc'd for C23H27N7OSi: 445.2.

Workup

  1. customTo an argon flushed pressure vial (15 mL)
  2. customThe vial was sealed
  3. concentrationwas concentrated
  4. custompurified by MPLC (eluted with 0-10% (90:10:1 DCM:MeOH:NH4OH))

Sources & evidence

ORD record
ord-45f46bc8592143aca9aedbe6151ad6cd
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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