Hydrochloric Acid → HCID 67338108, compound

HRID 1909123Notes

Reaction equation

HRID 1909123 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:18]=1)[C:12]([O:14]C)=[O:13].[OH-].[Na+].Cl>CC(N(C)C)=O>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:18]=1)[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67338283HCID 67338283, compound

Product 1

HCID 67338108HCID 67338108, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of methyl 2-(2-fluoro-4-methylphenyl)-6-morpholin-4-ylisonicotinate (0.31 g, 0.94 mmol) in DMA (4 mL) was added sodium hydroxide (1.0 M solution in water; 1.87 mL, 1.87 mmol). The mixture was stirred at ambient temperature. After 1 h, HCl (1.0 Min water; 1.87 mL, 1.87 mmol) was added and the mixture was concentrated. Methanol was added and the mixture was filtered and the filtrate was concentrated. The mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid). HCl (1.0 M) was added and fractions were concentrated to give the hydrochloride salt of the title compound (129 mg). MS 317.0 (M+1).

Workup

  1. concentrationthe mixture was concentrated
  2. additionMethanol was added
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)
  6. additionHCl (1.0 M) was added
  7. concentrationfractions were concentrated

Sources & evidence

ORD record
ord-c0d0870212e04c20a87b7f0f233cd697
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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