HCID 86670371, compound → HCID 86670372, compound

HRID 1972501Notes

Reaction equation

HRID 1972501 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=3)[C@@H:12]([CH2:32][CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH2:11]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1>CCO.[Pd]>[F:30][C:27]([F:28])([F:29])[C:22]([C:19]1[CH:20]=[N:21][C:16]([N:13]2[CH2:14][CH2:15][N:10]([S:7]([C:5]3[S:6][CH:2]=[CH:3][CH:4]=3)(=[O:9])=[O:8])[CH2:11][C@@H:12]2[CH2:32][CH:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[N:17][CH:18]=1)([OH:31])[C:23]([F:24])([F:26])[F:25]

Participants

4

Reactant 1

HCID 86670371HCID 86670371, compound

Product 1

HCID 86670372HCID 86670372, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 50-mL round-bottomed flask a mixture of (S)-2-(2-(4-(5-bromothiophen-2-ylsulfonyl)-2-((tetrahydro-2H-pyran-4-yl)methyl)piperazin-1-yl)pyrimidin-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol (60 mg, 0.092 mmol) and 10% Pd/C (19.5 mg, 0.018 mmol) in EtOH (10 mL) stirred under 1 atm of H2 for 8 h. Afterwards, the mixture was filtered through a pad of Celite® (diatomaceous earth). The filtrate was concentrated and the crude product was purified by carefully filtering through a plug of silica gel using 5% MeOH in CH2Cl2 as the eluent. Concentration of the filtrate yielded 1,1,1,3,3,3-hexafluoro-2-(2-((2S)-2-(tetrahydro-2H-pyran-4-ylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)-5-pyrimidinyl)-2-propanol (32 mg).

Workup

  1. filtrationAfterwards, the mixture was filtered through a pad of Celite® (diatomaceous earth)
  2. concentrationThe filtrate was concentrated
  3. customthe crude product was purified
  4. filtrationby carefully filtering through a plug of silica gel using 5% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-e537a0e88f20427ba10dd3308cb73d52
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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