Sodium Methoxide → HCID 57932981, compound

HRID 1432688Notes

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].[CH3:29][O-:30].[Na+]>[Cu]I.CO>[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[O:30][CH3:29])=[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: 130 °C

Procedure

100 mg of 3-(4-Bromo-2-morpholin-4-yl-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.22 mmol), 24 mg of sodium methoxide (0.44 mmol) and 21 mg of CuI (0.11 mmol) are put into 4 ml vial with MeOH 3 ml and capped with a Teflon® lined cap. The reaction vial is heated at 130° C. overnight. The reaction mixture is concentrated and applied onto a silica-gel chromatography column (Hexane: THF=10:1) to give 32.8 mg of the title compound. Yield 36%. Mass spectrum (m/e): 416 (M+1). 1H NMR (CDCl3): δ 6.64 (s, 1H), 3.96 (s, 3H), 3.86 (t, J=4.7 Hz, 4H), 3.53 (m, 4H), 3.34 (m, 1H), 2.82 (s, 3H), 2.48 (s, 3H), 1.82 (m, 4H), 0.85 (t, J=7.4 Hz, 6H).

Workup

customlined cap
customThe reaction
concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record: ord-4f094e0d3da34a4aaafbc2f268d14a65
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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