Triethylamine → HCID 68849360, compound

HRID 1723814Notes

Reaction equation

HRID 1723814 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][CH2:8][CH:9](O)[CH2:10][S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[CH:22][N:21]=2)[CH2:16][CH2:15]1)(=[O:13])=[O:12].CS(Cl)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[F:30][C:28]([F:29])([F:31])[CH2:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([N:17]2[CH2:16][CH2:15][N:14]([S:11](/[CH:10]=[CH:9]/[CH2:8][CH2:7][C:2]3[N:3]=[CH:4][CH:5]=[CH:6][N:1]=3)(=[O:13])=[O:12])[CH2:19][CH2:18]2)=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68847044HCID 68847044, compound

Product 1

HCID 68849360HCID 68849360, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of the 4-pyrimidin-2-yl-1-({4-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]piperazin-1-yl}sulfonyl)butan-2-ol (13.7 g, 28.8 mmol) in DCM (250 mL) at 0° C. was added methanesulfonyl chloride (2.68 mL, 34.6 mmol). The reaction was stirred at 0° C. for 20 minutes before dropwise addition of triethylamine (18.1 mL, 129 mmol). Warmed to room temperature and stirred for 16 hours. The reaction mixture was then diluted with DCM (1 L), washed with water (150 mL) and dried (brine, MgSO4), filtered and concentrated in vacuo. The residue was then purified by flash chromatography (silica, 0-5% MeOH in DCM) to give 2-[(3E)-4-({4-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]piperazin-1-yl}sulfonyl)but-3-en-1-yl]pyrimidine as a yellow solid (11.9 g, 18.6 mmol, 90%).

Workup

  1. washwashed with water (150 mL)
  2. dry with materialdried (brine, MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was then purified by flash chromatography (silica, 0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-5d36e1cb3b7943948f89082c459c7c92
Source dataset
uspto-grants-2009_02
Patent number
US07485644B2

Reaction notes

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