Sodium Hydroxide → HCID 59140183, compound

HRID 2076184Notes

Reaction equation

HRID 2076184 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-00dcccbffecc4073828c5ee662840288
Source dataset
uspto-grants-2011_04
Patent number
US07923456B2

Reaction notes

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