Pyridine → HCID 25019282, compound

HRID 1785617Notes

Reaction equation

HRID 1785617 reaction equation
[NH2:1][N:2]1[CH2:6][C@@H:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:4]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:3]1=[O:25].N1C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH3:32][S:33]([NH:1][N:2]1[CH2:6][C@@H:5]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)[N:4]([CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:3]1=[O:25])(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 68427132HCID 68427132, compound

Product 1

HCID 25019282HCID 25019282, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-amino-3-[2-(4-methoxyphenyl)-ethyl]-4-(R)-(4-methoxyphenyl)-2-imidazolidinone (247 g, 0.72 mol) in dichloromethane (2.35 L) and pyridine (174 mL, 2.15 mol) is cooled in an ice bath to 18° C. Methanesulfonyl chloride (73 mL, 0.94 mol) is added dropwise. The reaction is stirred cold for 2.5 hours then washed with 0.5 N HCl (2×1.5 L), brine (2×1.5 L) and dried (Na2SO4). The solvent is then removed in vacuo to afford a mixture of the desired product (75%) and unreacted starting material (25%) which is separated by liquid chromatography. [α]20D −39.83 (c 0.89, CHCl3) 1H NMR (300 MHz, CDCl3) δ 7.16 (d, J=8.81, 2H, ArH), 7.02 (d, J=8.51, 2H, ArH), 6.91 (d, J=8.81, 2H, ArH), 6.80 (d, J=8.81, 2H, ArH), 4.41 (m, 1H), 3.92 (m, 1H), 3.82 (s, 3H, CH3), 3.77 (s, 3H, CH3), 3.60-3.72 (m, 1H), 3.30 (m, 1H), 3.03 (s, 3H, CH3), 2.87-2.98 (m, 1H), 2.53-2.79 (m, 3H). MS 418 (MH+). Anal. Calcd. for C21H27N3O4S¼H2O: C, 59.77, H, 6.57; N, 9.96. Found: C, 59.82, H, 6.06; N, 9.85. FAB-HRMS: anal. calcd for C21H27N3O4S: 418.18005. Found: 418.17960.

Workup

  1. washthen washed with 0.5 N HCl (2×1.5 L), brine (2×1.5 L)
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is then removed in vacuo
  4. customto afford

Sources & evidence

ORD record
ord-b34076ae389d4507b8b9606ddb0eccac
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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