Benzenesulfonic Acid → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine benzenesulfonic acid

HRID 1432697Notes

Reaction equation

HRID 1432697 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]=[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].[C:30]1([S:36]([OH:39])(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CO>[C:30]1([S:36]([OH:39])(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[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 7371Benzenesulfonic AcidHCID 579329538-(1-Ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine

Product 1

HCID 866200958-(1-Ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine benzenesulfonic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 8-(1-ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine (0.23 g, 0.57 mmol) and MeOH (1 mL) is added a solution of benzenesulfonic acid (0.096 g, 0.57 mmol) and MeOH (1 mL). The solution is concentrated to furnish the title compound (0.32 g, 0.57 mmol, >99%). 1H NMR (CDCl3) δ 0.79 (t, J=7.0 Hz, 6H), 1.59-1.82 (m, 4H), 2.06 (s, 3H), 2.61 (s, 6H), 2.88 (s, 3H), 3.22-3.32 (m, 1H), 6.79 (bs, 2H), 7.25 (s, 1H), 7.33-7.42 (m, 3H), 7.49 (d, J=7.9 Hz, 1H), 7.80 (d, J=7.4 Hz, 2H), 7.92 (dd, J=7.4, 1.6 Hz, 1H) 8.23 (s, 1H). LC/MS (m/z): calcd. for C24H28N4S (M+H)+: 405.2; found: 405.4.

Workup

  1. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-488e0ad9d95d44eb8e4d43c15c74cb32
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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