Water → Ambrisentan

HRID 1854783Notes

Reaction equation

HRID 1854783 reaction equation
[OH:1][C@@H:2]([C:6]([O:19][CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O-:5])=[O:4].Cl[C@H](C1C=CC(Cl)=CC=1)C[NH3+].CC(C)([O-])C.[Na+].[CH3:38][C:39]1[CH:44]=[C:43]([CH3:45])[N:42]=[C:41](S(C)(=O)=O)[N:40]=1.O>CN(C=O)C>[CH3:45][C:43]1[CH:44]=[C:39]([CH3:38])[N:40]=[C:41]([O:1][C@@H:2]([C:6]([O:19][CH3:20])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]([OH:5])=[O:4])[N:42]=1

Participants

6

Reactant 4

HCID 962WaterHCID 27723824,6-Dimethyl-2-methylsulfonylpyrimidineHCID 23676156Sodium t-butoxideHCID 86668129(R)-2,4-dichlorophenylethyl ammonium (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionate

Product 1

HCID 6918493Ambrisentan

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 25 mL three neck flask with stirring arrangement, (1 gm) (R)-2,4-dichlorophenylethyl ammonium (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionate and (0.622 gm) sodium tertiary butoxide (6.488 mmol) in 10 ml DMF at 25° C. were taken and stirred for 5 min. (0.604 gm) 4,6-dimethyl-2-(methylsulfonyl)pyrimidine (3.244 mmol) was added to the reaction mixture in one lot. The reaction mixture was stirred at room temperature for 4 hours and subsequently dumped into cold water and aqueous layer was washed with toluene. Aqueous layer was collected and acidified with HCl to adjust pH to 2. Solid white material was precipitated. Solid white material was precipitated. The solid so obtained was filtered, washed with water and dried.

Workup

  1. additionwas added to the reaction mixture in one lot
  2. washwas washed with toluene
  3. customAqueous layer was collected
  4. customSolid white material was precipitated
  5. customSolid white material was precipitated
  6. customThe solid so obtained
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-05d505829b234320a1ec76f18191e8c4
Source dataset
uspto-grants-2015_02
Patent number
US08962832B2

Reaction notes

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