Sodium Hydroxide → HCID 59140183, compound

HRID 1500698Notes

Reaction equation

HRID 1500698 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([F:23])[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:23][C:7]1[C:8]2[N:9]([CH:20]=[N:21][CH:22]=2)[C:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[F:19])=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 591401198-Fluoro-5-(2-fluoro-4-iodo-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester

Product 1

HCID 59140183HCID 59140183, compoundYield 90%

Conditions

Temperature
65 °C

Procedure

To a solution of 8-fluoro-5-(2-fluoro-4-iodo-phenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester (500 mg, 1.17 mmol) in IMS (10 mL) was added sodium hydroxide (1.75 mL, 1M aqueous solution, 1.75 mmol), the reaction mixture heated at 65° C. for 45 min. The reaction mixture was concentrated in vacuo and the residue taken up in water. 1N HCl was added to adjust to pH 1. The precipitate formed was filtered off and dried in vacuo to give the title compound (435 mg, 90%). LCMS (method B): RT=3.47 min, [M+H]+=416.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. addition1N HCl was added
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f2512001b1324af8bca7ce652dee44bf
Source dataset
uspto-grants-2015_12
Patent number
US09206174B2

Reaction notes

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