Cesium carbonate → HCID 57932968, compound

HRID 1432679Notes

Reaction equation

Br[C:2]1[S: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:24]([O-:27])([O-])=O.[Cs+].[Cs+]>C1COCC1>[CH2:18]([CH:17]([C:16]1[C:11]2[N:12]([C:8]([C:4]3[S:3][C:2]([N:10]4[CH2:11][CH2:16][C:24](=[O:27])[CH2:8][CH2:9]4)=[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

Conditions

Temperature: 110 °C

Procedure

100 mg of 3-(2-bromo-4-methyl-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.25 mmol), 182 mg of 4-piperidineethylene ketal (1.27 mmol) and 244 mg of Cs2CO3 (0.75 mmol) are put into 4.0 ml vial with 2.0 ml of THF. The vial is capped with a Teflon® lined cap and heated at 110° C. for 3 days. The reaction mixture is concentrated and applied onto a silica-gel chromatography column (Hexane:AcOEt=3:1) to give 116 mg of the title compound. Yield 100%. mass spectrum (m/e): 456 (M+1). 1H NMR (CDCl3): δ 6.69 (s, 1H), 4.05 (s, 4H), 3.70 (t, J=6.2 Hz, 4H), 3.35 (m, 1H), 2.56 (s, 3H), 2.46 (s, 3H), 2.18 (s, 3H), 1.90-1.78 (m, 8H), 0.90 (t, J=7.2 Hz, 6H).

Workup

customlined cap
concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record: ord-ecc884daa03448b99a5bf71c2ac1a989
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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