Sodium Hydroxide → HCID 67215462, compound

HRID 1677582Notes

Reaction equation

HRID 1677582 reaction equation
[OH-:1].[Na+].[NH2:3][C:4]1[CH:22]=[CH:21][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]#[N:20])[N:11]=2)=[O:9])=[CH:6][C:5]=1[O:23][CH3:24]>C(O)C>[NH2:3][C:4]1[CH:22]=[CH:21][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]([NH2:20])=[O:1])[N:11]=2)=[O:9])=[CH:6][C:5]=1[O:23][CH3:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67215261HCID 67215261, compound

Product 1

HCID 67215462HCID 67215462, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.4 ml (26.4 mmol) of 6N aqueous sodium hydroxide solution are added to 0.5 g (1.7 mmol) of 3-(4-amino-3-methoxybenzoyl)imidazo[1,5-a]pyridine-1-carbonitrile obtained in example 85 in 50 ml of ethanol under a nitrogen atmosphere. After heating at reflux for 2 hours, the reaction medium is concentrated under reduced pressure. The residue obtained is washed with water, with acetone and with ethyl ether and then dried. 0.447 g of a yellow solid is collected. The product is salified by addition of a 1N solution of hydrochloric acid in ethyl ether. 0.310 g of a yellow solid is obtained. Melting point: 241° C.; 1H NMR (d6-DMSO): 3.89 (3H, s), 6.74 (1H, d), 7.24-7.27 (1H, m), 7.45-7.49 (1H, m), 7.88 (1H, s), 8.33 (1H, d), 8.42 (1H, d), 9.65 (1H, d)

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 hours
  3. concentrationthe reaction medium is concentrated under reduced pressure
  4. customThe residue obtained
  5. washis washed with water, with acetone and with ethyl ether
  6. customdried
  7. custom0.447 g of a yellow solid is collected
  8. additionThe product is salified by addition of a 1N solution of hydrochloric acid in ethyl ether

Sources & evidence

ORD record
ord-8a7b0f9fa9b743bf97a0b4ecd57e4f02
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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