Sodium Hydroxide → HCID 59140130, compound

HRID 2076167Notes

Reaction equation

HRID 2076167 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:22]=[N:23][CH:24]=2)[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:20][CH2:19]2)=[CH:14][C:13]=1[F:21])=[O:4].[OH-].[Na+]>CO>[F:21][C:13]1[CH:14]=[C:15]([CH:18]2[CH2:19][CH2:20]2)[CH:16]=[CH:17][C:12]=1[NH:11][C:10]1[N:9]2[CH:22]=[N:23][CH:24]=[C:8]2[CH:7]=[CH:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 591401405-(2-Fluoro-4-cyclopropylphenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester

Product 1

HCID 59140130HCID 59140130, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-(2-fluoro-4-cyclopropylphenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester (573 mg, 1.73 mmol) in methanol (20 mL) was added aqueous sodium hydroxide (10 mL, 1M, 10 mmol) and the reaction mixture stirred at 70° C. for 30 minutes. The reaction mixture was concentrated in vacuo to ˜20 mL volume and the resultant solution diluted with water (20 mL) and filtered. The filtrate was acidified to pH ˜1 by addition of aqueous hydrochloric acid (1M) causing a precipitate to form. The precipitate was collected by filtration and dried under vacuum at 45° C. to yield the title compound as a dark tan solid (476 mg, 87%). LCMS (Method B): RT=2.81 min, M+H+=318.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to ˜20 mL volume
  2. additionthe resultant solution diluted with water (20 mL)
  3. filtrationfiltered
  4. additionThe filtrate was acidified to pH ˜1 by addition of aqueous hydrochloric acid (1M)
  5. customto form
  6. filtrationThe precipitate was collected by filtration
  7. customdried under vacuum at 45° C.

Sources & evidence

ORD record
ord-a67a4215678044ffaefbd4aa36bace1c
Source dataset
uspto-grants-2011_04
Patent number
US07923456B2

Reaction notes

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