Dimethylamine → HCID 57932993, compound

HRID 1432728Notes

Reaction equation

HRID 1432728 reaction equation
Br[C:2]1[S:3][C:4]([C:11]2[N:15]3[N:16]=[C:17]([CH3:25])[CH:18]=[C:19]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[C:14]3=[N:13][C:12]=2[CH3:26])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:33][NH:34][CH3:35]>C1COCC1>[CH2:21]([CH:20]([C:19]1[C:14]2[N:15]([C:11]([C:4]3[S:3][C:2]([N:34]([CH3:35])[CH3:33])=[N:6][C:5]=3[C:7]([F:10])([F:9])[F:8])=[C:12]([CH3:26])[N:13]=2)[N:16]=[C:17]([CH3:25])[CH:18]=1)[CH2:23][CH3:24])[CH3:22]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 10796Cesium carbonateHCID 68840477HCID 68840477, compound

Product 1

HCID 57932993HCID 57932993, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

100 mg of 3-(2-Bromo-4-trifluoromethyl-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.22 mmol) and 218 mg of cesium carbonate (0.66 mmol) are placed in 4 ml reaction vial and 3 ml of dimethylamine 2 M in THF is added. The reaction vial is capped with a Teflon cap and heated at 120° C. overnight. The reaction mixture is filtered and concentrated and applied onto a silica-gel chromatography column (Hexane:AcOEt=3:1) to give 85 mg of the title compound. Yield 94%. mass spectrum (m/e): 412 (M+1).

Workup

  1. customThe reaction
  2. customcap
  3. filtrationThe reaction mixture is filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-960584bfc1ce4a119bbc623cc2a9064d
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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