Sodium Methoxide → (E)-2-(2-(6-Chloro-8-morpholino-3-(pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)vinyl)quinoline-5-carboxylic acid sodium salt

HRID 718694Notes

Reaction equation

HRID 718694 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[C:5]2[N:6]([C:8]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[C:9](/[CH:11]=[CH:12]/[C:13]3[CH:22]=[CH:21][C:20]4[C:19]([C:23]([OH:25])=[O:24])=[CH:18][CH:17]=[CH:16][C:15]=4[N:14]=3)[N:10]=2)[N:7]=1.C[O-].[Na+:40]>CO>[Na+:40].[Cl:1][C:2]1[CH:3]=[C:4]([N:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)[C:5]2[N:6]([C:8]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[C:9](/[CH:11]=[CH:12]/[C:13]3[CH:22]=[CH:21][C:20]4[C:19]([C:23]([O-:25])=[O:24])=[CH:18][CH:17]=[CH:16][C:15]=4[N:14]=3)[N:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 117728468(E)-2-(2-(6-Chloro-8-morpholino-3-(pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)vinyl)quinoline-5-carboxylic acid

Product 1

HCID 117728470(E)-2-(2-(6-Chloro-8-morpholino-3-(pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)vinyl)quinoline-5-carboxylic acid sodium salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To compound 73g (31.3 mg, 0.061 mmol) in MeOH (0.6 mL) was added NaOMe (0.12 mL, 0.061 mmol). The resulting mixture was stirred for 30 min and the solvent was removed in vacuo to obtain a solid which was then dried at 70° C. under high vacuum to afford the title compound 140 as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.47 (d, J=8.8 Hz, 1H), 8.89 (s, 1H), 8.74 (d, J=3.9 Hz, 1H), 8.15 (d, J=7.6 Hz, 1H), 7.53-7.87 (m, 7H), 6.57 (s, 1H), 4.22 (br. s., 4H), 3.86 (br. s., 4H). Mass spectrum (LCMS, ESI pos.) Calcd. For C27H21ClN6O3: 513.1 (M+H). Found 512.8.

Workup

  1. customthe solvent was removed in vacuo
  2. customto obtain a solid which
  3. customwas then dried at 70° C. under high vacuum

Sources & evidence

ORD record
ord-71d5da245a6e4b308060816d6aa847de
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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