Triethylamine → HCID 58042856, compound

HRID 564137Notes

Reaction equation

HRID 564137 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[CH:13][C:12]2=[O:25])=[CH:5][CH:4]=1.[CH2:26]([N:28](CC)[CH2:29][CH3:30])[CH3:27].CS(Cl)(=O)=O.N1CCCC1>C(Cl)Cl>[N:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][C:14]2[CH:15]=[CH:16][N:11]([CH2:10][CH2:9][C:6]3[CH:5]=[CH:4][C:3]([CH2:2][N:28]4[CH2:29][CH2:30][CH2:27][CH2:26]4)=[CH:8][CH:7]=3)[C:12](=[O:25])[CH:13]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31268PyrrolidineHCID 31297Methanesulfonyl chloride2×HCID 67006678HCID 67006678, compound

Product 1

HCID 58042856HCID 58042856, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 45 mg (0.13 mmol) 1-[2-(4-hydroxymethyl-phenyl)-ethyl]-4-(pyridin-4-ylmethoxy)-1H-pyridin-2-one (example 10.1a) in 3.0 mL DCM is added at RT 56 μL (0.40 mmol) triethylamine and subsequently 21 μL (0.27 mmol) methanesulfonyl chloride. The reaction mixture is stirred 1 h at RT. Additional 56 μL triethylamine (0.40 mmol) and subsequently 21 μL (0.27 mmol) methanesulfonyl chloride are added at RT and the reaction mixture is stirred for additional 1.5 h. Then 22 μL (0.27 mmol) pyrrolidine is added. The mixture is stirred overnight at RT, diluted with 50 mL DCM and is washed four times with water. The organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via chromatography (silica gel; DCM/MeOH/NH4OH 9:1:0.1 to 8:2:0.2).

Workup

  1. stirringthe reaction mixture is stirred for additional 1.5 h
  2. stirringThe mixture is stirred overnight at RT
  3. washis washed four times with water
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. customThe residue is purified via chromatography (silica gel; DCM/MeOH/NH4OH 9:1:0.1 to 8:2:0.2)

Sources & evidence

ORD record
ord-470a59c7ce474dd28d5588a75dadc3b0
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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