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Pyridine → HCID 67230439, compound

HRID 386482
Notes
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Reaction equation

HRID 386482 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[CH:10][C:11]([F:20])=[C:12]([N:14]3[CH2:18][CH2:17][CH2:16][C:15]3=[O:19])[CH:13]=2)=[CH:4][CH:3]=1.[CH3:23][N:24]1[CH:28]=[C:27]([S:29](Cl)(=[O:31])=[O:30])[N:26]=[CH:25]1.N1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]([C:8]2[CH:9]=[CH:10][C:11]([F:20])=[C:12]([N:14]3[CH2:18][CH2:17][CH2:16][C:15]3=[O:19])[CH:13]=2)[S:29]([C:27]2[N:26]=[CH:25][N:24]([CH3:23])[CH:28]=2)(=[O:31])=[O:30])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 67230285HCID 67230285, compound

Product 1

HCID 67230439HCID 67230439, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[5-(4-Chloro-benzylamino)-2-fluoro-phenyl]-pyrrolidin-2-one (32 mg, 0.1 mmol), 1-methylimidazole-4-sulfonyl chloride (54 mg, 0.3 mmol) and pyridine (24 ul, 0.3 mmol) were refluxed in dry dichloromethane (3 ml) for 18 hrs. The reaction mixture was concentrated in vacuo and the residue purified by preparative HPLC to afford the title compound as a yellow oil (19.5 mg, 42%). HPLC retention time 4.3 min, Mass spectrum (ES+) m/z 464 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-ff15d49494d44957b21d53a016302edf
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372840B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes