Triethylamine → 4-(Pyridin-2-ylmethoxy)-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one

HRID 564109Notes

Reaction equation

HRID 564109 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][CH:22]=[CH:21][N: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:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][O:17][C:14]1[CH:15]=[CH:16][N:11]([CH2:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:28]3[CH2:29][CH2:30][CH2:27][CH2:26]3)=[CH:4][CH:5]=2)[C:12](=[O:25])[CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 31297Methanesulfonyl chlorideHCID 670066931-[2-(4-hydroxymethylphenyl)-ethyl]-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 580427064-(Pyridin-2-ylmethoxy)-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 150 mg (0.45 mmol) 1-[2-(4-hydroxymethyl-phenyl)-ethyl]-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one in 5.0 mL DCM is added 186 μL (1.34 mmol) triethylamine and subsequently 69 μL (0.89 mmol) methanesulfonyl chloride at RT. The reaction mixture is stirred 1 h at RT and 74 μL (0.89 mmol) pyrrolidine is added. The mixture is stirred overnight at RT and is directly transferred to a reverse HPLC for purification (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).

Workup

  1. stirringThe mixture is stirred overnight at RT
  2. customis directly transferred to a reverse HPLC for purification (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90)

Sources & evidence

ORD record
ord-2c25233c223b4e7b8ec8aadb6afc62e7
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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