Methyl iodide → HCID 69011848, compound

HRID 1432685Notes

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]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[N:15][C:14]=3[CH3:24])=[C:10]([CH3:12])[N:11]=[C:4]2[C:3]=1[CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27].[Li][CH2:31]CCC.CCCCCC.IC>CCOCC>[Br:1][C:2]1([CH3:31])[C:7]([CH3:8])=[N:6][N:5]2[CH:9]([C:13]3[S:17][C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[N:15][C:14]=3[CH3:24])[C:10]([CH3:12])=[N:11][C:4]2=[C:3]1[CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27]

Participants

Conditions

Temperature: -78 °C

Procedure

50 mg of N-{5-[7-Bromo-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-4-methyl-thiazol-2-yl}-morpholine (0.1 mmol) is dissolved in 4 ml of Et2O and cooled to −78° C. 0.09 ml of n-BuLi 1.6M in hexane (0.15 mmol) is added at −78° C. and stirred at −78° C. for 20 min. 43 mg of iodomethane (0.3 mmol) is added to the mixture and stirred at −78° C. and allowed to come to room temperature overnight. The reaction is quenched with sat. NH4Cl and extracted with Et2O. The separated organic layer is dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt=3:1) to give 29.6 mg of the title compound. Yield 69%. mass spectrum (m/e): 414 (M+1). 1H NMR (CDCl3): δ 3.87 (t, J=4.6 Hz, 4H), 3.56 (t, J=4.6 Hz, 4H), 3.35 (m, 1H), 2.54 (s, 3H), 2.43 (s, 3H), 2.35 (s, 3H), 2.20 (s, 3H), 2.01 (m, 4H), 0.88 (m, 6H).

Workup

stirringstirred at −78° C.
waitto come to room temperature overnight
customThe reaction is quenched with sat. NH4Cl
extractionextracted with Et2O
dry with materialThe separated organic layer is dried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-2ba78faecdb84737bced5deec23d1b97
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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