Potassium Carbonate → HCID 57654489, compound

HRID 1921614Notes

Reaction equation

HRID 1921614 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[CH:8][C:9]3[N:10]([C:12]([CH2:15][C:16]4[CH:17]=[C:18]5[C:23](=[CH:24][CH:25]=4)[N:22]=[CH:21][CH:20]=[CH:19]5)=[N:13][N:14]=3)[N:11]=2)[CH:3]=[N:2]1.C([O-])([O-])=O.[K+].[K+].[CH3:32][O:33][CH2:34][CH2:35]Br>CCO>[CH3:32][O:33][CH2:34][CH2:35][N:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[CH:8][C:9]3[N:10]([C:12]([CH2:15][C:16]4[CH:17]=[C:18]5[C:23](=[CH:24][CH:25]=4)[N:22]=[CH:21][CH:20]=[CH:19]5)=[N:13][N:14]=3)[N:11]=2)[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 135925278HCID 135925278, compound

Product 1

HCID 57654489HCID 57654489, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-[6-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl]-quinoline as prepared in Example 3 (19 mg, 0.06 mmol) and K2CO3 (12 mg, 0.09 mmol) in EtOH (2 mL) was added 2-bromoethyl methyl ether (8 μL, 0.09 mmol). The reaction was stirred at rt overnight. The reaction was concentrated in vacuo followed by purification by HPLC (5-65% CH3CN over 35 min) resulting in the title compound (2.8 mg, 15%) as a clear glass. 1H-NMR (CD3OD): δ 9.05-9.03 (1H, dd, J=3.7, 5.3 Hz), 9.02-8.99 (1H, d, J=7.8 Hz), 8.32 (1H, s), 8.27 (1H, s), 8.18-8.08 (4H, m), 7.95-7.91 (1H, q, J=3.0, 5.5 Hz), 7.66-7.63 (1H, d, J=9.8 Hz), 4.84 (2H, s), 4.30-4.28 (2H, t, 4.8 Hz), 3.70-3.76 (2H, t, J=5.3 Hz), 3.23 (2H, br s). ESI-MS (m/z): Calcd. For C21H19N7O: 385.17; found: 386.2 (M+H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customfollowed by purification by HPLC (5-65% CH3CN over 35 min)

Sources & evidence

ORD record
ord-ff49f1339a5e46c4aed1d89c4a21acbe
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

Loading…