Acetyl chloride → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine hydrochloride

HRID 1432588Notes

Reaction equation

HRID 1432588 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([Cl:33])(C)=O>CO>[ClH:33].[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 6367Acetyl chlorideHCID 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 688439288-(1-Ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine hydrochlorideYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using a procedure similar to Example 33, 8-(1-ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine (0.55 g, 1.36 mmol), MeOH (6 mL) and AcCl (0.098 mL, 1.36 mmol) furnish the title compound (0.11 g, 0.25 mmol, 42%). 1H NMR (CDCl3), δ 0.96 (t, J=7.2 Hz, 6H), 1.74-1.89 (m, 2H), 1.89-2.02 (m, 2H), 2.22 (s, 3H), 2.68 (s, 3H), 2.78 (s, 3H), 3.08 (s, 3H), 3.88-3.98 (m, 1H), 7.23 (s, 1H), 7.40 (d, J=6.9 Hz, 1H), 7.71 (d, J=4.8 Hz, 1H), 8.06 (s, 1H), 8.82 (s, 1H). LC/MS (m/z): calcd. for C24H29ClN4S (M+H)+: 441.3; found: 405.2.

Sources & evidence

ORD record
ord-8a01e319871a42b18dc6b093fce3c2f0
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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