Sodium Carbonate → HCID 58190496, compound

HRID 456180Notes

Reaction equation

HRID 456180 reaction equation
[CH3:1][C:2]1([C:7]2[CH:8]=[N:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[N:23]=[CH:22][CH:21]=[CH:20]5)=[CH:14][N:15]=3)[N:12]=2)OCC[O:3]1.C([O-])([O-])=O.[Na+].[Na+]>Cl>[N:23]1[C:24]2[C:19](=[CH:18][C:17]([CH2:16][C:13]3[N:11]4[N:12]=[C:7]([C:2](=[O:3])[CH3:1])[CH:8]=[N:9][C:10]4=[N:15][CH:14]=3)=[CH:26][CH:25]=2)[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 58190569HCID 58190569, compound

Product 1

HCID 58190496HCID 58190496, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 6-((2-(2-methyl-1,3-dioxolan-2-yl)imidazo[1,2-b][1,2,4]triazin-7-yl)methyl)quinoline (130 mg, 0.37 mmol) in 3 N HCl (5 mL) was stirred at 90° C. for 0.5 h. The reaction mixture was cooled to room temperature, neutralized with saturated aqueous Na2CO3 solution, extracted with ethyl acetate, dried over Na2SO4. The solvent was removed in vacuo to afford 85 mg (75%) of the title compound as yellow solid. 1H-NMR (400 MHz, CDCl3) δ ppm 9.06 (s, 1H), 8.91 (d, 1H), 8.12 (t, 2H), 8.04 (s, 1H), 7.74-7.71 (m, 2H), 7.48-7.39 (m, 1H), 4.60 (s, 2H), 2.70 (s, 3H). LCMS (method B): [MH]+=304, tR=1.81 min.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a86b4573338e4d1ba8f0fc6e552d36b1
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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