p-Toluenesulfonic acid monohydrate → HCID 178433271, compound

HRID 2080992Notes

Reaction equation

HRID 2080992 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[CH2:10][NH:11][C:12]([CH:14]1[CH2:18][NH:17][C:16](=[O:19])[N:15]1[CH3:20])=[O:13].Cl.[CH3:22][C:23]1[N:24]=[CH:25][NH:26][C:27]=1[CH2:28]O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN1CCCC1=O.ClCCl>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[CH2:10][NH:11][C:12]([CH:14]1[CH2:18][N:17]([CH2:28][C:27]2[NH:26][CH:25]=[N:24][C:23]=2[CH3:22])[C:16](=[O:19])[N:15]1[CH3:20])=[O:13]

Participants

6

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 25098282N-[(2-Chloro-3,4-difluorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamideHCID 178433279HCID 178433279, compound

Product 1

HCID 178433271HCID 178433271, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (152 mg, 0.5 mmol) (prepared as described in Example 28), (4-methyl-1H-imidazol-5-yl)methanol hydrochloride (93 mg, 0.625 mmol) and p-toluene sulfonic acid monohydrate (19 mg, 0.100 mmol) in N-methyl-2-pyrrolidone (1 ml) was heated at 130° C. under argon for 3 h. The reaction mixture was cooled to room temperature and diluted with dichloromethane. The solution was washed with saturated sodium hydrogen carbonate solution and brine, dried and evaporated. The residue was purified by mass-directed automated HPLC, followed by trituration with ether to give N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1-[(4-methyl-1H-imidazol-5-yl)methyl]-2-oxo-4-imidazolidinecarboxamide (147 mg, 74%). LC/MS [M+H]+=398, retention time=1.57 minutes.

Workup

  1. washThe solution was washed with saturated sodium hydrogen carbonate solution and brine
  2. customdried
  3. customevaporated
  4. customThe residue was purified

Sources & evidence

ORD record
ord-07145fe5a9d647ceb0743b1767052f77
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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