Ethyl Acetate → HCID 57933053, compound

HRID 1432686Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[S:5][C:6]=1[C:7]1[N:11]2[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]2=[N:9][C:8]=1[CH3:22].[F:29][C:30]([F:35])([F:34])C([O-])=O.[Na+].CCOC(C)=O>CN(C=O)C.C1(C)C=CC=CC=1.[Cu]I.CCCCCC.C(Cl)Cl.CC#N>[CH2:17]([CH:16]([C:15]1[C:10]2[N:11]([C:7]([C:6]3[S:5][C:4]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[N:3][C:2]=3[C:30]([F:35])([F:34])[F:29])=[C:8]([CH3:22])[N:9]=2)[N:12]=[C:13]([CH3:21])[CH:14]=1)[CH2:19][CH3:20])[CH3:18]

Participants

Conditions

Temperature: 210 °C

Procedure

170 mg of 3-(4-Bromo-2-morpholin-4-yl-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.37 mmol) and 100 mg of sodium trifluoroacetate (0.74 mmol) are dissolved in 3 ml of DMF/toluene=2/1. N2 gas is bubbled into the mixture for 20 min and 141 mg of CuI (0.74 mmol) is added. The vial is sealed and heated in the microwave at 210° C. for 30 min. The reaction mixture is applied onto a silica-gel chromatography column (Hexane:AcOEt=3:1 and CH3CN:CH2Cl2:Hexane=5:45:50) to give 64.3 mg of the title compound. Yield 38%. mass spectrum (m/e): 454 (M+1). 1H NMR (CDCl3): δ 6.72 (s, 1H), 3.88 (m, 4H), 3.60 (m, 4H), 3.32 (m, 1H), 2.54 (s, 3H), 2.47 (s, 3H), 1.85 (m, 4H), 0.89 (t, J=7.0 Hz, 6H).

Workup

customN2 gas is bubbled into the mixture for 20 min
customThe vial is sealed

Sources & evidence

ORD record: ord-06bd896497974d26b890963f8b535c15
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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