Dimethylamine → N-{5-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-4-methyl-oxazol-2-yl}-dimethylamine

HRID 1432597Notes

Reaction equation

HRID 1432597 reaction equation
Br[C:2]1[O:3][C:4]([C:8]2[N:12]3[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]3=[N:10][C:9]=2[CH3:23])=[C:5]([CH3:7])[N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:30][NH:31][CH3:32]>C1COCC1>[CH2:18]([CH:17]([C:16]1[C:11]2[N:12]([C:8]([C:4]3[O:3][C:2]([N:31]([CH3:32])[CH3:30])=[N:6][C:5]=3[CH3:7])=[C:9]([CH3:23])[N:10]=2)[N:13]=[C:14]([CH3:22])[CH:15]=1)[CH2:20][CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 10796Cesium carbonateHCID 688409823-(2-Bromo-4-methyl-oxazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Product 1

HCID 57932997N-{5-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-4-methyl-oxazol-2-yl}-dimethylamineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

32 mg of 3-(2-Bromo-4-methyl-oxazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.08 mmol) and 78 mg of cesium carbonate (0.24 mmol) are placed into vial with 3 ml of dimethylamine 2.0 M in THF. The vial is capped with a Teflon cap and heated at 110° C. for 3 days. The reaction mixture is cooled to room temperature, concentrated, and applied onto a silica-gel chromatography column (Hexane:AcOEt:2M NH3 in MeOH=10:2:1) to give 24 mg of the title product. Yield 89%. mass spectrum (m/e): 342 (M+1). 1H-NMR (CDCl3): 6.71 (s, 1H), 3.34 (m, 1H), 3.13 (s, 6H), 2.56 (s, 3H), 2.49 (s, 3H), 2.14 (s, 3H), 1.84 (m, 4H), 0.89 (t, J=7.5 Hz, 6H).

Workup

  1. customcap
  2. temperatureThe reaction mixture is cooled to room temperature
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8df59019b96241ee8d006ebeb1448870
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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