Sodium hydride → HCID 58742325, compound

HRID 1988096Notes

Reaction equation

HRID 1988096 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C@@:9]1([OH:27])[C@@H:22]([OH:23])[CH2:21][C@:20]2([CH2:24][CH3:25])[C@H:11]([CH2:12][CH2:13][C:14]3[C:19]2=[CH:18][CH:17]=[C:16]([OH:26])[CH:15]=3)[CH2:10]1.[H-].[Na+].Cl.Cl[CH2:32][C:33]1[C:34]([CH3:39])=[N:35][CH:36]=[CH:37][CH:38]=1.[Cl-].[NH4+]>CN(C)C=O.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C@@:9]1([OH:27])[C@@H:22]([OH:23])[CH2:21][C@:20]2([CH2:24][CH3:25])[C@H:11]([CH2:12][CH2:13][C:14]3[C:19]2=[CH:18][CH:17]=[C:16]([O:26][CH2:32][C:33]2[C:34]([CH3:39])=[N:35][CH:36]=[CH:37][CH:38]=2)[CH:15]=3)[CH2:10]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 122437123-(CHLOROMETHYL)-2-METHYLPYRIDINE HYDROCHLORIDEHCID 58742299HCID 58742299, compound

Product 1

HCID 58742325HCID 58742325, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the compound of Example 35 (35 mg, 0.093 mmol), sodium hydride 60% (20 mg, 0.5 mmol) and 3-chloromethyl-2-methyl-pyridine hydrochloride (23 mg, 0.13 mmol) in 3 mL of dimethylformamide (DMF) was stirred overnight. Saturated aqueous ammonium chloride solution (5 mL) and water (15 mL) were added and the mixture extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to a oil (35 mg). The residue was purified by flash chromatography using a 50% to 80% ethyl acetate / hexanes eluant to afford 20 mg (44%) of the title compound as an oil, which was crystallized from hexanes to give a white solid. Melting point: 80-83° C. Mass spectrum: (m/e) 461 (M+−H2O, +ion).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×20 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a oil (35 mg)
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fdb9b68bba5d4e83b4e6603896dec7bc
Source dataset
uspto-grants-2009_06
Patent number
US07553877B2

Reaction notes

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