Dimethyl Sulfoxide → HCID 58688073, compound

HRID 2266694Notes

Reaction equation

HRID 2266694 reaction equation
CS(C)=O.[CH2:5]([OH:7])[CH3:6].[H-].[Na+].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:49])[C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[N:32][C:33]([NH2:48])=[C:34]([O:36][CH:37]([C:39]4[C:44]([Cl:45])=[CH:43][CH:42]=[C:41](F)[C:40]=4[Cl:47])[CH3:38])[CH:35]=3)=[CH:26][CH:25]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:49])[C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[N:32][C:33]([NH2:48])=[C:34]([O:36][CH:37]([C:39]4[C:44]([Cl:45])=[CH:43][CH:42]=[C:41]([O:7][CH2:5][CH3:6])[C:40]=4[Cl:47])[CH3:38])[CH:35]=3)=[CH:26][CH:25]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 702EthanolHCID 24758Sodium hydrideHCID 59599422HCID 59599422, compound

Product 1

HCID 58688073HCID 58688073, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To 4 mL of DMSO was added 0.124 ml ethanol followed by 32 mg NaH. After stirring for 30 minutes 250 mg of 250 mg 4-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester was added and the reaction was heated to 40° C. After three hours the reaction was cooled and poured into water to precipitate. After neutralization to pH 6, 200 mg of a tan solid was isolated, 77%.

Workup

  1. additionwas added
  2. temperatureAfter three hours the reaction was cooled
  3. customto precipitate

Sources & evidence

ORD record
ord-85980e5eebc84b56ae6eea06a27584b0
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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