Sodium Hydroxide → HCID 67215871, compound

HRID 1677583Notes

Reaction equation

HRID 1677583 reaction equation
[OH-].[Na+].C([NH:11][C:12]1[CH:20]=[CH:19][C:18]([C:21]([C:23]2[N:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]3=[C:25]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[N:24]=2)=[O:22])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])(=O)C1C=CC=CC=1.S([O-])(O)(=O)=O.[K+]>O1CCOCC1>[NH2:11][C:12]1[CH:20]=[CH:19][C:18]([C:21]([C:23]2[N:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]3=[C:25]([C:32]3[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=3)[N:24]=2)=[O:22])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 67215636HCID 67215636, compound

Product 1

HCID 67215871HCID 67215871, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1.2 g of sodium hydroxide pellets are added to 0.259 g (0.5 mmol) of 2-benzoylamino-5-{[1-(4-methoxyphenyl)imidazo[1,5-a]pyridin-3-yl]carbonyl}benzoic acid obtained in example 155 in solution in 25 ml of dioxane. The mixture is heated at reflux for 48 hours. The reaction medium is allowed to return to ambient temperature. The medium is taken up in dioxane and then acidified with potassium hydrogensulfate. The precipitate formed is filtered off, then rinsed with water and dried. 0.162 g of a yellow solid is collected, which solid is salified in the sodium salt.1.15H2O form. Melting point: 296° C.; 1H NMR (d6-DMSO): 3.85 (3H, s), 6.63 (1H, d), 7.09-7.17 (3H, m), 7.28-7.35 (1H, m), 7.96 (2H, d), 8.17 (1H, d), 8.34 (1H, d), 9.04 (1H, s), 9.69 (1H, d)

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 48 hours
  3. customto return to ambient temperature
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washrinsed with water
  7. customdried
  8. custom0.162 g of a yellow solid is collected

Sources & evidence

ORD record
ord-9aeb79d257c048559c32cd6a0e8d1836
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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