Dimethyl Sulfoxide → HCID 9823875, compound

HRID 1068012Notes

Reaction equation

HRID 1068012 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:25][CH:24]([OH:26])[CH2:23]4)[CH:17]=3)[N:12]([CH3:27])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(C)=[O:39]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:23][C:24]([OH:39])([OH:26])[CH2:25]4)[CH:17]=3)[N:12]([CH3:27])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 21192602HCID 21192602, compound

Product 1

HCID 9823875HCID 9823875, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(4-chlorobenzyl)-6-[(3-hydroxy-1-azetidinyl)methyl]-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.10 gm) from Example No. 75 in dry DMSO (3 mL) containing triethylamine (0.35 mL) is treated with pyridine-sulfar trioxide complex (0.25 gm). The reaction mixture is stirred at room temperature for 2 hrs. The reaction mixture is diluted with ethyl acetate and washed with water (2×), brine, dried (Na2SO4) and concentrated under reduced pressure. The residue is purified by recrysrallization from acetonitrile to afford 0.06 gm of the title compound as a tan solid.

Workup

  1. additionis treated with pyridine-sulfar trioxide complex (0.25 gm)
  2. washwashed with water (2×), brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by recrysrallization from acetonitrile

Sources & evidence

ORD record
ord-af480280a1c8448fad2b549b6571ca19
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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