Hydrochloric Acid → HCID 56941127, compound

HRID 1844027Notes

Reaction equation

HRID 1844027 reaction equation
Cl.C([N:5]1[C:17]2[CH:16]=[C:15]3[C:10]([CH2:11][CH2:12][N:13]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][C:24]=4[CH3:25])[C:14]3=[O:18])=[CH:9][C:8]=2[CH:7]=[N:6]1)(=O)C.C(OCC)(=O)C>CO>[CH3:25][C:24]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N:13]1[CH2:12][CH2:11][C:10]2[C:15](=[CH:16][C:17]3[NH:5][N:6]=[CH:7][C:8]=3[CH:9]=2)[C:14]1=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 89964093HCID 89964093, compound

Product 1

HCID 56941127HCID 56941127, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6N HCl (5 mL) was added drop wise to a solution of 1-acetyl-7-(4-methylpyridin-3-yl)-6,7-dihydro-1H-pyrazolo[4,3-g]isoquinolin-8(5H)-one (I-69h: 80 mg, 0.249 mmol) in methanol (5 ml) at 0° C. and the resulting reaction mass was stirred at room temperature for 36 hours. The reaction was monitored by TLC (100% ethyl acetate). The reaction mass was concentrated under reduced pressure, basified using saturated NaHCO3 solution and extracted using ethyl acetate. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (100% ethyl acetate), followed by preparative HPLC afforded 8 mg of the product (11.5% yield).

Workup

  1. customthe resulting reaction mass
  2. concentrationThe reaction mass was concentrated under reduced pressure
  3. extractionextracted
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (100% ethyl acetate)

Sources & evidence

ORD record
ord-b27796adb9b7425fa7b7c50ec805e11f
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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