Isobutylamine → HCID 70656238, compound

HRID 1972578Notes

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

Participants

Reactant 4

HCID 6558Isobutylamine

HCID 31297Methanesulfonyl chloride

HCID 665827271,1,1-trifluoro-2-(4-((2S)-2-(((2-methylpropyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

HCID 86670301((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate2×

Product 1

HCID 70656238HCID 70656238, 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 isobutyl amine (Aldrich, St. Louis, Mo.), followed by sulfonamide formation (using MsCl) delivered 1,1,1-trifluoro-2-(4-((2S)-2-(((2-methylpropyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol as a mixture of two isomers.

Workup

customThis compound was synthesized
additionas a mixture of two isomers

Sources & evidence

ORD record: ord-d45fd6ffa79846b582e09fa4500e223a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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