N-methyl-2-pyrrolidone → 3-Quinolin-6-ylmethyl-imidazo[1,2-b]pyridazine-6-carbonitrile

HRID 69248Notes

Reaction equation

HRID 69248 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[CH:9][N:10]=2)[N:7]=1.[C:21]([Cu])#[N:22].[CH3:24]N1C(=O)CCC1>CCOC(C)=O>[N:12]1[C:13]2[C:14](=[CH:24][C:20]([CH2:11][C:8]3[N:6]4[N:7]=[C:2]([C:21]#[N:22])[CH:3]=[CH:4][C:5]4=[N:10][CH:9]=3)=[CH:19][CH:18]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 44206294(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-quinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 579173223-Quinolin-6-ylmethyl-imidazo[1,2-b]pyridazine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-quinoline (Example 14) (50 mg, 0.17 mmol) and CuCN (23 mg, 0.26 mmol) in 0.5 mL NMP were heated under microwave irradiation at 230° C. for 9.5 h. The RM was diluted with EtOAc and washed with aqueous saturated NaHCO3 and brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA) to yield the title compound as a yellow solid (tR 2.16 min (conditions 8), MH+=286).

Workup

  1. washwashed with aqueous saturated NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA)

Sources & evidence

ORD record
ord-e5b9edf2872c43308c805818c8337249
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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