Dichloromethane → HCID 56832521, compound

HRID 1972345Notes

Reaction equation

HRID 1972345 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].C(Cl)Cl.C(N(CC)CC)C.[S:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[S:38](Cl)(=[O:40])=[O:39]>O>[F:22][C:2]([F:1])([F:21])[C:3]([C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([S:38]([C:34]3[S:33][CH:37]=[CH:36][CH:35]=3)(=[O:40])=[O:39])[CH2:17][CH2:16]2)=[CH:13][CH:14]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 866237611,1,1,3,3,3-Hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol

Product 1

HCID 56832521HCID 56832521, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round-bottomed flask was charged with 1,1,1,3,3,3-hexafluoro-2-(4-(1-piperazinyl)phenyl)-2-propanol (2.27 g, 6.92 mmol, published PCT patent application no. WO 2006/094842), 20 mL of CH2Cl2 and triethylamine (1.45 mL, 10.4 mmol). To this was added 2-thiophenesulfonyl chloride (1.39 mL, 7.61 mmol, Sigma-Aldrich, St. Louis, Mo.) and the mixture was stirred at room temperature for 2 h. After that time, the mixture was diluted with water (50 mL) and extracted with EtOAc (100 mL). The combined extracts were dried (MgSO4) and concentrated. This oil was purified by column chromatography (120 g silica gel, 0 to 50% EtOAc in hexanes) to give 1,1,1,3,3,3-hexafluoro-2-(4-(4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (2.35 g) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.70-7.65 (m, 1H) 7.64-7.56 (m, 3H), 7.23-7.18 (m, 1H), 7.02-6.94 (m, 2H), 3.43-3.36 (m, 4H), 3.33-3.25 (m, 4H). m/z (ESI, +ve ion) 475.0 (M+H)+. GK-GKRP EC50 (NADPH-coupled)=0.332 μM; GK-GKRP EC50 (LC MS/MS)=0.500 μM.

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customThis oil was purified by column chromatography (120 g silica gel, 0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7d26dec01980437a9f515b9549c3ee88
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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