Hydrochloric Acid → HCID 10269434, compound

HRID 586376Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:22][CH3:23])=[C:9]([CH2:11][N:12]3[CH:16]=[CH:15][N:14]=[C:13]3[C:17]3[S:18][CH:19]=[CH:20][N:21]=3)[N:10]=2)[N:7]=1.[CH2:24]([O:26]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:25].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH2:22]([C:8]1[N:6]2[N:7]=[C:2]([C:24](=[O:26])[CH3:25])[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[C:17]1[S:18][CH:19]=[CH:20][N:21]=1)[CH3:23]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6-chloro-3-ethyl-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-imidazo[1,2-b]pyridazine (100 mg, 0.26 mmol), 1-ethoxyvinyltributylstannane (142 mg, 0.39 mmol) and PdCl2(Ph3P)2 (10 mg) in anhydrous toluene (5 mL) is heated at 110° C. in a sealed tube for 5 hours. On cooling, water (2 mL), and concentrated HCl (2 mL) are added and the mixture is stirred at room temperature for 2 hours. The mixture is neutralized with sodium carbonate solution and extracted with methylene chloride (3×15 mL). The combined organic layers are dried (Na2SO4) and the solvent removed. The residue is purified by PTLC (5% methanol in methylene chloride) to give 1-[3-ethyl-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)imidazo[1,2-b]pyridazin-6-yl]ethanone as a solid. 1H NMR (CDCl3): 7.95, d (1H); 7.86, d (1H0; 7.70, d (1H); 7.36, d (1H); 7.25, d (1H); 7.11, d (1H); 6.18, s (2H); 3.10, q (2H); 2.75, s (3H); 1.18, t (3H).

Workup

temperatureOn cooling
extractionextracted with methylene chloride (3×15 mL)
dry with materialThe combined organic layers are dried (Na2SO4)
customthe solvent removed
customThe residue is purified by PTLC (5% methanol in methylene chloride)

Sources & evidence

ORD record: ord-af25a079698340e88a800181c845b665
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936617B2

Reaction notes

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