Dichloromethane → HCID 67215756, compound

HRID 1677585Notes

Reaction equation

HRID 1677585 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]=[C:16]([C:19]([O:21]C)=[O:20])[CH:17]=[CH:18][C:13]3=[CH:12][N:11]=2)=[O:9])=[CH:6][C:5]=1[O:25][CH3:26].O1CCOCC1.ClCCl>CO>[NH2:3][C:4]1[CH:24]=[CH:23][C:7]([C:8]([C:10]2[N:14]3[CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=[CH:18][C:13]3=[CH:12][N:11]=2)=[O:9])=[CH:6][C:5]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 67216356HCID 67216356, compound

Product 1

HCID 67215756HCID 67215756, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.51 ml (1.51 mmol) of a 1N aqueous sodium hydroxide solution are added to 300 mg (0.92 mmol) of methyl 3-(4-amino-3-methoxybenzoyl)imidazo[1,5-a]pyridine-6-carboxylate obtained in example 83 in 15 ml of a mixture (5/5/5) of dioxane, dichloromethane and methanol. The reaction medium is stirred at ambient temperature overnight and then concentrated under reduced pressure. The residue is dissolved in water, washing is carried out with ethyl acetate and then the aqueous phase is acidified with 1.5 ml of 1N hydrochloric acid. The precipitate formed is filtered off, washed with water and then dried. 346 mg of a yellow solid are collected, which solid is salified in the sodium salt.0.7H2O form. Melting point: 306° C.; 1H NMR (d6-DMSO): 3.87 (3H, s), 6.72 (1H, d), 7.70-7.78 (3H, m), 7.96 (1H, s), 8.18 (1H, d), 10.09 (1H, s)

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue is dissolved in water
  3. washwashing
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water
  7. customdried
  8. custom346 mg of a yellow solid are collected
  9. customform

Sources & evidence

ORD record
ord-f727fea716e74283a5dc647fe9729527
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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