Hydrochloric Acid → HCID 59651983, compound

HRID 887056Notes

Reaction equation

HRID 887056 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[N:7][N:6](COC)[C:5](=[O:12])[C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][C@H:24]2[CH3:28])=[CH:15][CH:14]=1.Cl.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[N:7][NH:6][C:5](=[O:12])[C:4]=1[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][C@H:24]2[CH3:28])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 59652019HCID 59652019, compound

Product 1

HCID 59651983HCID 59651983, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round-bottom flask was added example 231 (5-Methoxy-2-methoxymethyl-4-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-2H-pyridazin-3-one) (1.07 g, 2.76 mmol), methanol (10 mL), and concentrated HCl solution (10 mL). The reaction was heated to reflux for 3 days. After cooled to room temperature, the reaction was neutralized with 10 N NaOH then 5% NaOH solution to pH 7. The reaction was concentrated and the residue was washed with CH2Cl2 (100 mL). The CH2Cl2 layer was concentrated. Purification by column chromatography (15% MeOH in CH2Cl2) to give 350 mg (37%) of 5-methoxy-4-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-2H-pyridazin-3-one. The product was converted to its hydrochloride salt. Mp 135-140. MS m/z 344 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 days
  3. concentrationThe reaction was concentrated
  4. washthe residue was washed with CH2Cl2 (100 mL)
  5. concentrationThe CH2Cl2 layer was concentrated
  6. customPurification by column chromatography (15% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-66bb6e6f47e94a729932725bff830dbe
Source dataset
uspto-grants-2012_08
Patent number
US08247414B2

Reaction notes

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