2-(Dimethylamino)ethanol → 2-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-3-methyl-benzo[b]thiophen-5-ol

HRID 226114Notes

Reaction equation

HRID 226114 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][C:24](F)=[CH:25][C:19]=4[C:18]=3[CH3:27])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[OH-].[K+].CN(C)CC[OH:34]>CS(C)=O.C(OCC)(=O)C.O>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][C:24]([OH:34])=[CH:25][C:19]=4[C:18]=3[CH3:27])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

7

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 14797Potassium HydroxideHCID 577525998-(1-Ethyl-propyl)-2,6-dimethyl-3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-imidazo[1,2-b]pyridazine

Product 1

HCID 577527042-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-3-methyl-benzo[b]thiophen-5-olYield 25.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

In an oven dried, nitrogen purged pressure tube, 0.040 g (0.105 mmol) of 8-(1-ethyl-propyl)-3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine, 0.012 g (0.21 mmol) of KOH, and 0.019 g (0.210 mmol) of N,N-dimethylethanolamine are combined in 1 mL of dry DMSO and heated at 90° C. After approximately 24 hours, the reaction mixture is diluted with 20 mL of ethyl acetate and 20 mL of water. The layers are separated and the aqueous is extracted 3×50 mL of ethyl acetate, dried (MgSO4), and concentrated under vacuum. The crude mixture is purified by chromatography using Hexane/Ethyl Acetate. The product containing fractions are combined to obtain 0.010 g of the title compound, 25% yield. MS, ES+=380.1 (M+1); 1H NMR (DMSO-d6)=9.518 (s, 1H); 7.760-7.730 (s, 1H); 7.129 (s, 1H); 6.980 (s, 1H); 3.150-3.050 (m, 1H); 2.421 (s, 3H); 2.336 (s, 3H); 2.103 (s, 3H); 1.850-1.760 (m, 4H); 0.789-0.753 (m, 6H) ppm.

Workup

  1. customIn an oven dried
  2. customnitrogen purged pressure tube
  3. customThe layers are separated
  4. extractionthe aqueous is extracted 3×50 mL of ethyl acetate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customThe crude mixture is purified by chromatography
  8. additionThe product containing fractions

Sources & evidence

ORD record
ord-dc0e8cb85ca242cdb0ae6c49222071da
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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