Morpholine → HCID 68841975, compound

HRID 1432660Notes

Reaction equation

HRID 1432660 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20](Br)=[N:19][C:18]=3[CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[N:19][C:18]=3[CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 68840065HCID 68840065, compound

Product 1

HCID 68841975HCID 68841975, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

110 mg of 8-(1-ethyl-propyl)-3-[2-bromo-4-methyl-5-thiazolyl]-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.28 mmol) and 122 mg of morpholine (1.4 mmol) are dissolved in 3.0 ml of THF and 182 mg of cesium carbonate (0.56 mmol) is added. The mixture is put in 4 ml vial with a Teflon® lined cap and heated at 110 C overnight. The reaction mixture is concentrated and applied to a silica-gel column chromatography column with hexane:EtOAc=3:1 eluent to give 98 mg of the title compound (88%). mass spectrum (m/e): 400 (M+1); 1H-NMR (CDCl3): δ 6.70 (s, 1H), 3.87 (t, 4H, J=4.8 Hz), 3.56 (t, 4H, J=4.8 Hz), 3.35 (m, 1H) 2.56 (s, 3H), 2.46 (s, 3H), 1.86 (m, 4H), 0.90 (t, 6H, J=7.6 Hz)

Workup

  1. customlined cap
  2. temperatureheated at 110 C overnight
  3. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-e9ea563ebc774fd285c78c038588aac2
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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