Hydrochloric Acid → HCID 59278221, compound

HRID 1361204Notes

Reaction equation

HRID 1361204 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH:11]([NH:14][C:15]([C:17]2[C:18]3[CH:25]=[N:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:19]=3[CH:20]=[N:21][CH:22]=2)=[O:16])[CH2:12][CH3:13])[O:8][C:9]=1[CH3:10])=[O:4].O[Li].O.Cl>C1COCC1.CO.O>[F:32][C:29]1[CH:28]=[CH:27][C:26]([N:23]2[C:19]3[CH:20]=[N:21][CH:22]=[C:17]([C:15]([NH:14][CH:11]([C:7]4[O:8][C:9]([CH3:10])=[C:5]([C:3]([OH:4])=[O:2])[N:6]=4)[CH2:12][CH3:13])=[O:16])[C:18]=3[CH:25]=[N:24]2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59278232HCID 59278232, compound

Product 1

HCID 59278221HCID 59278221, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 2-(1-{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-propyl)-5-methyl-oxazole-4-carboxylic acid methyl ester (95.0 mg, 0.217 mmol) in a mixture of THF/Methanol/water (3 mL, 3:1:1) was added LiOH.H2O (36.5 mg, 0.869 mmol). After 3 hours, the reaction mixture was acidified to pH 3-4 with 2 M aqueous hydrochloric acid and concentrated. The mixture was diluted with ethyl acetate (25 mL) and water (25 mL) and stirred vigorously. After 5 hours, the heterogeneous mixture was filtered and the solid was washed with water (until the pH of the filtrate was 5), ethyl acetate (3×10 mL), and air dried to afford the title compound as a white solid. MS m/z 424.74 (MH+).

Workup

  1. concentrationconcentrated
  2. additionThe mixture was diluted with ethyl acetate (25 mL) and water (25 mL)
  3. waitAfter 5 hours
  4. filtrationthe heterogeneous mixture was filtered
  5. washthe solid was washed with water (until the pH of the filtrate
  6. customdried

Sources & evidence

ORD record
ord-12871d437c804cfca856e9640e7d4410
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Reaction notes

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