Methanesulfonyl chloride → HCID 70655274, compound

HRID 1972579Notes

Reaction equation

HRID 1972579 reaction equation
CS(OC[C@H]1CN(S(C2SC=CC=2)(=O)=O)CCN1C1C=CC(C(O)(C)C(F)(F)F)=CC=1)(=O)=O.C1(NC)CC1.[CH3:39][S:40](Cl)(=[O:42])=[O:41].[CH:44]1([CH2:47][NH:48][CH2:49][C@H:50]2[CH2:55][N:54]([S:56]([C:59]3[S:60][CH:61]=[CH:62][CH:63]=3)(=[O:58])=[O:57])[CH2:53][CH2:52][N:51]2[C:64]2[CH:69]=[CH:68][C:67]([C:70]([OH:76])([CH3:75])[C:71]([F:74])([F:73])[F:72])=[CH:66][CH:65]=2)[CH2:46][CH2:45]1>>[CH:44]1([CH2:47][N:48]([CH2:49][C@H:50]2[CH2:55][N:54]([S:56]([C:59]3[S:60][CH:61]=[CH:62][CH:63]=3)(=[O:58])=[O:57])[CH2:53][CH2:52][N:51]2[C:64]2[CH:69]=[CH:68][C:67]([C:70]([OH:76])([CH3:75])[C:71]([F:72])([F:73])[F:74])=[CH:66][CH:65]=2)[S:40]([CH3:39])(=[O:42])=[O:41])[CH2:45][CH2:46]1

Participants

5

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 11029756N-MethylcyclopropanamineHCID 706549142-(4-((2S)-2-(((cyclopropylmethyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanolHCID 86670301((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate2×

Product 1

HCID 70655274HCID 70655274, compound

Procedure

This compound was synthesized following the scheme described for Example 195. The reaction of ((2R)-4-(thiophen-2-ylsulfonyl)-1-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)piperazin-2-yl)methyl methanesulfonate (Intermediate B) and cyclopropyl methylamine (Alfa Aesar, Ward Hill, Mass.), followed by sulfonamide formation (using MsCl) delivered 2-(4-((2S)-2-(((cyclopropylmethyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol as a mixture of two isomers.

Workup

  1. customThis compound was synthesized
  2. additionas a mixture of two isomers

Sources & evidence

ORD record
ord-d042738d75f641ae8180e69ccd9d6e23
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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