Sodium Hydroxide → HCID 59140186, compound

HRID 1500678Notes

Reaction equation

HRID 1500678 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:20]=[N:21][CH:22]=2)[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=1[F:19])=[O:4].[OH-].[Na+]>>[F:19][C:13]1[CH:14]=[C:15]([I:18])[CH:16]=[CH:17][C:12]=1[NH:11][C:10]1[N:9]2[CH:20]=[N:21][CH:22]=[C:8]2[CH:7]=[CH:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 591401365-(2-Fluoro-4-iodophenylamino)imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester

Product 1

HCID 59140186HCID 59140186, compoundYield 100%

Conditions

Temperature
65 °C

Procedure

To a solution of 5-(2-fluoro-4-iodophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester (5.6 g, 13.6 mmol) in IMS (50 mL) was added aqueous sodium hydroxide (27.2 mL, 1M, 27.2 mmol) and the reaction mixture stirred at 65° C. for 2 hours. The reaction mixture was concentrated in vacuo to remove the IMS. The resultant solution was acidified to pH ˜5 by addition of aqueous hydrochloric acid (1M) causing a precipitate to form. The product was collected by filtration and dried under vacuum at 45° C. to yield the title compound as a beige solid (5.4 g, 100%). LCMS (Method B): RT=2.79 min, M+H+=398.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove the IMS
  3. additionThe resultant solution was acidified to pH ˜5 by addition of aqueous hydrochloric acid (1M)
  4. customto form
  5. filtrationThe product was collected by filtration
  6. customdried under vacuum at 45° C.

Sources & evidence

ORD record
ord-054d2fb44855498a87ea0f93d7a8bd25
Source dataset
uspto-grants-2015_12
Patent number
US09206174B2

Reaction notes

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