Morpholine → HCID 57933013, compound

HRID 1432664Notes

Reaction equation

[Br:1][C:2]1[C:7]([CH3:8])=[N:6][N:5]2[C:9]([C:13]3[S:17][C:16](Br)=[N:15][C:14]=3[CH3:19])=[C:10]([CH3:12])[N:11]=[C:4]2[C:3]=1[CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[Br:1][C:2]1[C:7]([CH3:8])=[N:6][N:5]2[C:9]([C:13]3[S:17][C:16]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[N:15][C:14]=3[CH3:19])=[C:10]([CH3:12])[N:11]=[C:4]2[C:3]=1[CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

72 mg of 7-bromo-3-(2-bromo-4-methyl-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.15 mmol) and 66 mg of morpholine (0.76 mmol) and 97 mg of cesium carbonate (0.3 mmol) are put in 4 ml vial with 3 ml of dry THF. The vial is capped with a Teflon® lined cap and heated at 100° C. overnight. The reaction mixture is concentrated and applied onto a silica-gel chromatography column (Hexane:AcOEt=3:1) to give 30 mg of the title compound. Yield 42%: mass spectrum (m/e): 479 (M+1); 1H-NMR (CDCl3): 3.87 (t, 4H, J=5.0 Hz), 3.55 (t, 4H, J=5.0 Hz), 3.45 (m, 1H), 2.70 (s, 3H), 2.44 (s, 3H), 2.40 (m, 2H), 2.18 (s, 3H), 2.01 (m, 2H), 0.88 (t, 6H, J=7.3 Hz).

Workup

customlined cap
concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record: ord-5d3f2623458045a39a92139e9770e3b0
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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