Acetylacetone → HCID 57933017, compound

HRID 1432671Notes

Reaction equation

[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]([NH:22][NH2:23])=[N:19][C:18]=3[CH3:24])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[CH3:25][C:26](=O)[CH2:27][C:28](=O)[CH3:29]>CC(O)=O>[CH3:25][C:26]1[CH:27]=[C:28]([CH3:29])[N:22]([C:20]2[S:21][C:17]([C:13]3[N:8]4[N:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]4=[N:15][C:14]=3[CH3:16])=[C:18]([CH3:24])[N:19]=2)[N:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

28 mg of {5-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-4-methyl-thiazol-2-yl}-hydrazine (0.08 mmol) and 80 mg of 2,4-pentanedione (0.8 mmol) are dissolved in 1.0 ml of AcOH and heated at 100° C. for 2 h. The reaction mixture is concentrated and applied onto a silica-gel chromatography column (Hexane:AcOEt=5:1) to give 23 mg of the title compound. Yield 70%: mass spectrum (m/e): 409 (M+1). 6.72 (s, 1H), 6.03 (s, 1H), 3.36 (m, J=7.1, 14.1 Hz, 1H), 2.75 (s, 3H), 2.55 (s, 3H), 2.50 (s, 3H), 2.32 (s, 3H), 2.31 (s, 3H), 1.87 (m, 4H), 0.91 (t, J=7.5 Hz, 6H).

Workup

concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record: ord-8f8489907f8543e1ab8fd07fabb3cdb2
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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