Triethylamine → HCID 86670392, compound

HRID 1972538Notes

Reaction equation

HRID 1972538 reaction equation
Cl.Cl.[F:3][C:4]([F:25])([F:24])[C:5]([C:11]1[CH:12]=[N:13][C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][C@@H:18]2[CH3:23])=[N:15][CH:16]=1)([OH:10])[C:6]([F:9])([F:8])[F:7].C(N(CC)CC)C.[N+:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[S:42](Cl)(=[O:44])=[O:43])([O-:35])=[O:34].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:25][C:4]([F:3])([F:24])[C:5]([C:11]1[CH:12]=[N:13][C:14]([N:17]2[CH2:22][CH2:21][N:20]([S:42]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[N+:33]([O-:35])=[O:34])(=[O:43])=[O:44])[CH2:19][C@@H:18]2[CH3:23])=[N:15][CH:16]=1)([OH:10])[C:6]([F:9])([F:8])[F:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86670343HCID 86670343, compound

Product 1

HCID 86670392HCID 86670392, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 15 mL round-bottomed flask was added 1,1,1,3,3,3-hexafluoro-2-(2-((2S)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-2-propanol dihydrochloride (0.28 g, 0.66 mmol, Example 89, Step 2), triethylamine (0.28 mL, 2.0 mmol) and CH2Cl2 (6 mL). To this solution at room temperature was added 2-nitrobenzenesulfonyl chloride (0.15 g, 0.66 mmol, Sigma-Aldrich, St. Louis, Mo.). The mixture was stirred at room temperature for 3 h and then saturated aqueous sodium bicarbonate was added. This was stirred for an additional 5 min and then the solution was transferred onto a phase separation cartridge (Radleys Discovery Technologies, Essex, UK) with the organic phase being collected. The collected solution was purified by silica gel chromatography (0 to 75% EtOAc in hexanes) to afford (S)-1,1,1,3,3,3-hexafluoro-2-(2-(2-methyl-4-(2-nitrophenylsulfonyl)piperazin-1-yl)pyrimidin-5-yl)-2-propanol (0.24 g) as a white solid.

Workup

  1. stirringThis was stirred for an additional 5 min
  2. customthe solution was transferred onto a phase separation cartridge (Radleys Discovery Technologies, Essex, UK) with the organic phase
  3. custombeing collected
  4. customThe collected solution was purified by silica gel chromatography (0 to 75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-416a0af9a1ac489fb2200438e81e0953
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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