Sodium Sulfate → HCID 67205372, compound

HRID 1894320Notes

Reaction equation

HRID 1894320 reaction equation
[NH2:1][C@@:2]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)([CH3:28])[C@@:3]([NH:12][C:13](=O)[C:14]1[C:19]([O:20][CH2:21][CH3:22])=[CH:18][C:17]([C:23]([CH3:26])([CH3:25])[CH3:24])=[N:16][CH:15]=1)([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)[CH3:4].P(Cl)(Cl)(Cl)=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C@@:2]2([CH3:28])[C@:3]([C:5]3[CH:6]=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=3)([CH3:4])[NH:12][C:13]([C:14]3[C:19]([O:20][CH2:21][CH3:22])=[CH:18][C:17]([C:23]([CH3:25])([CH3:24])[CH3:26])=[N:16][CH:15]=3)=[N:1]2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 24813Phosphorus oxychlorideHCID 68748854HCID 68748854, compound

Product 1

HCID 67205372HCID 67205372, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

rac-N-[(1S*,2R*)-2-Amino-1,2-bis-(4-chloro-phenyl)-1-methyl-propyl]-6-tert-butyl-4-ethoxy-nicotinamide (200 mg, 0.4 mmol) was dissolved in toluene (8 mL) and phosphorus oxychloride (0.2 mL, 0.83 mmol) was added. The reaction mixture was refluxed under nitrogen overnight. It was allowed to cool to room temperature and poured into ice water, basified with saturated solution of sodium sulfate (10 mL). Reaction mixture was extracted with ethyl acetate (2×20 ml) and methylene chloride (2×10 mL). The combined organic layers were washed with brine and water, dried with magnesium sulfate, filtered and evaporated. Purification was by chromatography (silica gel, eluting with 0-30% ethyl acetate/methylene chloride, then 5% methanol/methylene chloride) to give rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-2-tert-butyl-4-ethoxy-pyridine as a solid. (20 mg). LR-MS: 496 [(M+H)+]

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen overnight
  2. customReaction mixture
  3. extractionwas extracted with ethyl acetate (2×20 ml) and methylene chloride (2×10 mL)
  4. washThe combined organic layers were washed with brine and water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification
  9. washeluting with 0-30% ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-72994300217348de8e6e62fb00e4e760
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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