Sodium Hydroxide → HCID 67216236, compound

HRID 1677584Notes

Reaction equation

HRID 1677584 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:24]=[CH:23][C:7]([C:8]([C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[C:12]([C:19]([O:21]C)=[O:20])[N:11]=2)=[O:9])=[CH:6][C:5]=1[O:25][CH3:26].O1CCOCC1.S([O-])(O)(=O)=O.[K+]>CO>[NH2:3][C:4]1[CH:24]=[CH:23][C:7]([C:8]([C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[C:12]([C:19]([OH:21])=[O:20])[N:11]=2)=[O:9])=[CH:6][C:5]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 516920Potassium bisulfateHCID 67216189HCID 67216189, compound

Product 1

HCID 67216236HCID 67216236, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.67 ml (1.67 mmol) of a 1N aqueous sodium hydroxide solution are added to 0.272 g (0.84 mmol) of methyl 3-(4-amino-3-methoxybenzoyl)imidazo[1,5-a]pyridine-1-carboxylate obtained in example 150 in 12 ml of a mixture (1/1) of dioxane and methanol. After heating at reflux for 2 hours, the reaction medium is concentrated under reduced pressure. The residue is taken up in water and then acidified with 0.239 g (1.7 mmol) of potassium hydrogensulfate. The precipitate formed is filtered off, washed with water and ethyl ether, and dried. 0.22 g of an orange solid is collected, which solid is salified in the sodium salt.2.55H2O form. Melting point: 226° C.; 1H NMR (d6-DMSO): 3.86 (3H, s), 6.71 (1H, d), 7.06-7.11 (1H, m), 7.24-7.30 (1H, m), 7.89 (1H, s), 8.34 (1H, d), 8.59 (1H, d), 9.63 (1H, d)

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 hours
  3. concentrationthe reaction medium is concentrated under reduced pressure
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water and ethyl ether
  7. customdried
  8. custom0.22 g of an orange solid is collected
  9. customform

Sources & evidence

ORD record
ord-f0423f90668c4841877fd07bb4c9ff99
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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