Potassium Carbonate → N-((4-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-morpholinyl)methyl) methanesulfonamide

HRID 1972489Notes

Reaction equation

HRID 1972489 reaction equation
CS(O[CH2:6][C@H:7]1[CH2:12][N:11]([S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)(=O)=O.Cl.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH:36]1[CH2:41][NH:42][S:43]([CH3:46])(=[O:45])=[O:44].C(=O)([O-])[O-].[K+].[K+]>>[S:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[S:13]([N:11]1[CH2:10][CH2:9][N:8]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:25][CH:26]=2)[C@@H:7]([CH2:6][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH:36]2[CH2:41][NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH2:12]1)(=[O:14])=[O:15]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 68846716N-[(morpholin-3-yl)methyl]methanesulfonamide hydrochlorideHCID 86670301((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate2×

Product 1

HCID 56932473N-((4-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-morpholinyl)methyl) methanesulfonamide

Procedure

This compound was synthesized following the procedure outlined for Example 84. The reaction of ((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate (Intermediate B) and N-(3-morpholinylmethyl)methanesulfonamide hydrochloride (published PCT patent application no. WO 2009/016410) (using an extra equivalent of potassium carbonate) followed by purification via column chromatography on silica gel (0 to 100% EtOAc in hexanes) delivered N-((4-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-morpholinyl)methyl)methanesulfonamide as a mixture of four isomers.

Workup

  1. customThis compound was synthesized
  2. customfollowed by purification via column chromatography on silica gel (0 to 100% EtOAc in hexanes)
  3. additionas a mixture of four isomers

Sources & evidence

ORD record
ord-2c052282a8974e6c9395633ba99fc82b
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

Loading…