Sodium Hydroxide → 2,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid

HRID 2184307Notes

Reaction equation

HRID 2184307 reaction equation
S(O)(=O)(=O)C.[CH3:6][C:7]1[N:8]=[C:9]2[C:14]([NH:15][CH2:16][C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:24][CH3:25])=[CH:13][C:12]([C:26](N)=[O:27])=[CH:11][N:10]2[C:29]=1[CH3:30].[OH-:31].[Na+]>C(O)C>[CH3:6][C:7]1[N:8]=[C:9]2[C:14]([NH:15][CH2:16][C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:24][CH3:25])=[CH:13][C:12]([C:26]([OH:27])=[O:31])=[CH:11][N:10]2[C:29]=1[CH3:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 99106658-(2-Ethyl-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylate

Product 1

HCID 118239362,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acidYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,3-dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide mesylate (11.0 g, 0.025 mol) and sodium hydroxide (7.0 g, 0.17 mol) were solved in ethanol (95%) (120 ml) and was refluxed for 20 h. The solvent was evaporated under reduced pressure and to the residue was added water (50 ml). The pH was adjusted to 5 by addition of conc. HCl and acetic acid and the solid that precipitated was isolated by filtration, washed with water and acoetone, and dried to give 7.6 g (88%) of the title compound. 1H-NMR (500 MHz, DMSO-d6): δ 1.15 (t, 3H), 2.26 (s, 3H), 2.34 (s, 3H), 2.39 (s, 3H), 2.69 (q, 2H), 4.38 (d, 2H), 5.2 (bs, 1H), 6.73 (s, 1H), 7.07-7.2 (m, 3H), 8.12 (s, 1H)

Workup

  1. temperaturewas refluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure and to the residue
  3. additionwas added water (50 ml)
  4. additionThe pH was adjusted to 5 by addition of conc. HCl and acetic acid
  5. customthe solid that precipitated
  6. customwas isolated by filtration
  7. washwashed with water and acoetone
  8. customdried

Sources & evidence

ORD record
ord-db26543041ea45c1aa7020b030eb039d
Source dataset
uspto-grants-2005_05
Patent number
US06900324B2

Reaction notes

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