Sodium Methoxide → (E)-2-(2-(3-(3-methoxyphenyl)-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)vinyl)quinoline-5-carboxylic acid sodium salt

HRID 718702Notes

Reaction equation

HRID 718702 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:13]3[N:14]=[CH:15][CH:16]=[C:17]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:12]3=[N:11][C:10]=2/[CH:24]=[CH:25]/[C:26]2[CH:35]=[CH:34][C:33]3[C:32]([C:36]([OH:38])=[O:37])=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=2)[CH:6]=[CH:7][CH:8]=1.C[O-].[Na+:41]>>[Na+:41].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:13]3[N:14]=[CH:15][CH:16]=[C:17]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:12]3=[N:11][C:10]=2/[CH:24]=[CH:25]/[C:26]2[CH:35]=[CH:34][C:33]3[C:32]([C:36]([O-:38])=[O:37])=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 117728432(E)-2-(2-(3-(3-methoxyphenyl)-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)vinyl)quinoline-5-carboxylic acid

Product 1

HCID 117728541(E)-2-(2-(3-(3-methoxyphenyl)-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)vinyl)quinoline-5-carboxylic acid sodium salt

Procedure

Compound 77b (28 mg, 0.055 mmol) was treated with NaOMe (0.11 mL, 0.055 mmol) using the procedures described in Example 73, Step H to afford the title compound 149. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.99 (d, J=9.1 Hz, 1H), 7.92-8.04 (m, 3H), 7.87 (d, J=7.6 Hz, 1H), 7.59-7.79 (m, 3H), 7.49 (t, J=8.1 Hz, 1H), 7.22-7.35 (m, 2H), 7.08 (dd, J=7.8, 2.3 Hz, 1H), 6.23 (d, 1H), 4.07-4.12 (m, 4H), 3.93-3.99 (m, 4H), 3.88 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calcd. For C29H25N5O4 508.2 (M+H). found 508.3.

Sources & evidence

ORD record
ord-11f94697fc7f4b0280fad89ba42ce512
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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