Dipropylamine → HCID 57932978, compound

HRID 1432722Notes

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.[CH2:24]([NH:27][CH2:28][CH2:29][CH3:30])[CH2:25][CH3:26].C(=O)([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:27]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:25][CH3:26])=[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: 100 °C

Procedure

35 mg of 3-(2-Bromo-4-methyl-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.09 mmol) and 45 mg of di-n-propylamine (0.44 mmol) and 57 mg of cesium carbonate (0.18 mmol) are place into 4 ml reaction vial with 3 ml of dry THF and the vial is capped with a Teflon cap. The reaction vial is heated at 100° C. for 4 h. The reaction mixture is transferred into microwave reaction vessel and sealed. The reaction mixture is heated at 160° C. for 30 min by microwave. The mixture is concentrated and applied onto silica-gel chromatography column (Hexane:AcOEt=3:1) to give the title compound. 5.3 mg (14%); mass spectrum (m/e): 414; 1H-NMR (CDCl3): 5.59 (s, 1H), 3.45 (m, 4H), 3.36 (m, 1H), 2.57 (s, 3H), 2.47 (s, 3H), 2.17 (s, 3H), 1.80 (m, 8H), 0.99 (t, 6H, J=7.5 Hz), 0.89 (t, 6H, J=9.4 Hz).

Workup

customcap
customThe reaction
customThe reaction mixture is transferred into microwave reaction vessel
customsealed
temperatureThe reaction mixture is heated at 160° C. for 30 min by microwave
concentrationThe mixture is concentrated

Sources & evidence

ORD record: ord-99442bab7bb241b7be46d304cd2f7ec6
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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