Hydrochloric Acid → HCID 56832571, compound

HRID 920960Notes

Reaction equation

HRID 920960 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31](=[O:38])[NH:30][N:29]=2)=[CH:23][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]2[C:12]([C:19]([F:22])([F:21])[F:20])=[N:13][C:14]([C:15]([O:17]C)=[O:16])=[C:8]2[CH2:7]1)=[O:5].[OH-].[Na+].Cl>O1CCCC1.CO.O>[F:1][C:2]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31](=[O:38])[NH:30][N:29]=2)=[CH:23][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]2[C:12]([C:19]([F:20])([F:21])[F:22])=[N:13][C:14]([C:15]([OH:17])=[O:16])=[C:8]2[CH2:7]1)=[O:5]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 56833302HCID 56833302, compound

Product 1

HCID 56832571HCID 56832571, compoundYield 34.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 7-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoyl]-3-(trifluoromethyl)-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-1-carboxylate 3 (30 mg, 0.057 mmol) was dissolved in 1.5 mL of a mixed solvent of tetrahydrofuran, methanol and water (V N N=1:1:1), followed by addition of sodium hydroxide (10 mg, 0.25 mmol). After stirring for 12 hours, concentrated hydrochloric acid was added dropwise to the reaction mixture until the pH was 2. The reaction mixture was extracted with dichloromethane (15 mL×2). The organic phase was combined, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by thin layer chromatography with elution system A to obtain 7-[2-fluoro-5-[(4-oxo-3H-phthalazin-1-yl)methyl]benzoyl]-3-(trifluoromethyl)-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-1-carboxylic acid 8 (10 mg, yield 34.4%) as a light yellow solid.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (15 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by thin layer chromatography with elution system

Sources & evidence

ORD record
ord-c8668b63ed19483c9571c3a312dafdb1
Source dataset
uspto-grants-2016_03
Patent number
US09273052B2

Reaction notes

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