Methanesulfonic Acid → 2,6-Dimethyl-3-[3-methyl-5-(6-methyl-2-pyridinyl)thiophen-2-yl]-8-pentan-3-ylimidazo[1,2-b]pyridazine;methanesulfonic acid

HRID 1432699Notes

Reaction equation

HRID 1432699 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:20][C:21]=3[CH3:22])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[CH3:29][S:30]([OH:33])(=[O:32])=[O:31]>CO>[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=4)=[CH:20][C:21]=3[CH3:22])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 579329578-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-5-pyridin-2-yl-thiophen-2-yl)-imidazo[1,2-b]pyridazine

Product 1

HCID 866200972,6-Dimethyl-3-[3-methyl-5-(6-methyl-2-pyridinyl)thiophen-2-yl]-8-pentan-3-ylimidazo[1,2-b]pyridazine;methanesulfonic acidYield 200%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-(1-ethyl-propyl)-2,6-dimethyl-3-(3-methyl-5-pyridin-2-yl-thiophen-2-yl)-imidazo[1,2-b]pyridazine (0.55 g, 1.36 mmol) and MeOH (6 mL) is added methane sulfonic acid (0.088 mL, 1.36 mmol). After one hour the solution is concentrated and the solution is treated with Darco-60® for 1 hour, filtered and concentrated to furnish the title compound (0.68 g, 1.36 mmol, >99%). 1H NMR (CDCl3: CD3OD 95:5) δ 0.85 (t, J=7.4 Hz, 6H), 1.67-1.91 (m, 4H), 1.96 (s, 3H), 1.97 (s, 3H), 2.20 (s, 3H), 2.61 (s, 3H), 2.90 (s, 3H), 3.17-3.29 (m, 1H), 7.33 (s, 1H), 7.64 (d, J=7.4 Hz, 1H), 7.89 (d, J=7.9 Hz, 1H), 8.18 (s, 1H), 8.34 (t, J=7.9 Hz, 1H), 9.95 (bs, 1H). LC/MS (m/z): calcd. for C25H32N4O2S2 (M+H)+: 405.6; found: 405.6.

Workup

  1. concentrationAfter one hour the solution is concentrated
  2. additionthe solution is treated with Darco-60® for 1 hour
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1b9887269b9945439adb52fabfd031da
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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