1-Pentyn-3-ol → HCID 86670380, compound

HRID 1972520Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1.[CH:32]#[C:33][CH:34]([OH:37])[CH2:35][CH3:36]>>[S:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[S:14]([N:11]1[CH2:12][CH2:13][N:8]([C:7]2[CH:6]=[CH:5][C:4]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:3][C:2]=2[C:32]#[C:33][CH:34]([OH:37])[CH2:35][CH3:36])[CH2:9][CH2:10]1)(=[O:16])=[O:15]

Participants

Reactant 2

HCID 929811-Pentyn-3-ol

HCID 86670331HCID 86670331, compound

Product 1

HCID 86670380HCID 86670380, compound

Procedure

Following the procedure outlined for Example 152, 2-(3-bromo-4-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (Example 69) was coupled to 1-pentyn-3-ol (Aldrich, St. Louis, Mo.) to afford 1-(2-(4-(2-thiophenylsulfonyl)-1-piperazinyl)-5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-1-pentyn-3-ol as a mixture of enantiomers.

Sources & evidence

ORD record: ord-fa269371fab14f618466ea34e296af79
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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