Hydrochloric Acid → 8-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid

HRID 2067010Notes

Reaction equation

HRID 2067010 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[N:12][CH:13]=[C:7]2[C:6]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:23][CH2:22]2)=[CH:17][C:16]=1[F:24])=[O:4].[OH-].[Na+].Cl>>[CH:21]1([C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:6]3[C:7]4[N:8]([CH:11]=[N:12][CH:13]=4)[CH:9]=[CH:10][C:5]=3[C:3]([OH:4])=[O:2])=[C:16]([F:24])[CH:17]=2)[CH2:22][CH2:23]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 595651918-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester

Product 1

HCID 595651948-(4-Cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acidYield 82.2%

Conditions

Temperature
65 °C

Procedure

A suspension of 8-(4-cyclopropyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester (0.28 g, 0.86 mmol) and 1M NaOH (1.03 mL, 1.03 mmol) in IMS (5 mL) was heated to 65° C. for 5 hours. The reaction mixture was then cooled to room temperature and 1M HCl was added to adjust pH to 2. The precipitate formed was filtered off and dried in a drying pistol at 40° C. for 18 hours to afford the title compound as a cream solid (0.22 g, 81%). LCMS (method B): RT=2.84 min, [M+H]+=312.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. customdried in a drying pistol at 40° C. for 18 hours

Sources & evidence

ORD record
ord-3e3c9766f1f349eeb7bf76bee15e0413
Source dataset
uspto-grants-2012_10
Patent number
US08293763B2

Reaction notes

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