Sodium Hydroxide → HCID 67216304, compound

HRID 472929Notes

Reaction equation

HRID 472929 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][C:31]=1[NH:32][S:33]([CH2:36][CH2:37][CH3:38])(=[O:35])=[O:34])[C:8]([C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]2=[C:12]([C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=2)[C:22]([O:24]C)=[O:23])[N:11]=1)=[O:9]>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][C:31]=1[NH:32][S:33]([CH2:36][CH2:37][CH3:38])(=[O:35])=[O:34])[C:8]([C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]2=[C:12]([C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=2)[C:22]([OH:24])=[O:23])[N:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67215851HCID 67215851, compound

Product 1

HCID 67216304HCID 67216304, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

1.4 ml of a 1N aqueous sodium hydroxide solution are added to 0.34 g (0.7 mmol) of methyl 3-(3-{3-methoxy-4-[(propylsulfonyl)amino]benzoyl}imidazo[1,5-a]pyridin-1-yl)benzoate obtained in example 190 in 20 ml of methanol. The reaction medium is heated at 70° C. for 3 hours and then concentrated under reduced pressure. The residue is taken up in water and the aqueous phase obtained is washed with dichloromethane, neutralized by addition of 1.4 ml of 1N hydrochloric acid and then extracted with dichloromethane. The organic phase obtained is dried over sodium sulfate and concentrated under reduced pressure. 0.19 g of a yellow solid is collected, which solid is salified in the sodium salt.2.1H2O form. Melting point: 145° C.; 1H NMR (d6-DMSO): 0.96-1.01 (3H, t), 1.71-1.83 (2H, m), 3.16-3.19 (2H, m), 4.00 (3H, s), 7.33-7.70 (2H, m), 7.36-7.38 (1H, m), 7.52-7.97 (2H, m), 8.04-8.07 (2H, m), 8.27-9.85 (2H, m), 8.44 (1H, s), 8.64 (1H, s), 9.25 (1H, m)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe aqueous phase obtained
  3. washis washed with dichloromethane
  4. additionneutralized by addition of 1.4 ml of 1N hydrochloric acid
  5. extractionextracted with dichloromethane
  6. customThe organic phase obtained
  7. dry with materialis dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. custom0.19 g of a yellow solid is collected
  10. customform

Sources & evidence

ORD record
ord-efc8da5f9e2a4abc9901ab3ec27861eb
Source dataset
uspto-grants-2014_01
Patent number
US08633216B2

Reaction notes

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