Water → HCID 10303804, compound

HRID 347003Notes

Reaction equation

HRID 347003 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:35])([C:29]2[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=2)[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=[C:13]3[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)=[CH:5][CH:4]=1.[S:36]1[CH:40]=[CH:39][NH:38][C:37]1=[S:41].O>C1COCC1.C(N(CC)CC)C>[Cl:28][C:24]1[CH:23]=[C:22]([C:13]2[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([C:9]([OH:35])([C:29]4[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=4)[C:6]4[CH:5]=[CH:4][C:3]([CH2:2][S:41][C:37]5[S:36][CH:40]=[CH:39][N:38]=5)=[CH:8][CH:7]=4)[CH:11]=3)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1201387Thiazoline-2-thioneHCID 21082106(+/-)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4(3-chlorophenyl)-1-methyl-2(1H)-quinolinone

Product 1

HCID 10303804HCID 10303804, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of (±)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (0.0002 mol), obtained in Example B14, and 2(3H)-thiazolethione (0.001 mol) in THF (1 ml) and triethylamine (0.1 ml) was stirred at room temperature for 18 hours, poured out into water and extracted with CH2Cl2/CH3OH. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over kromasil 60 μm (eluent: CH2Cl2/CH3OH; 90/10). The pure fractions were collected and the solvent was evaporated, yielding (70%) of 4(3-chlorophenyl)-6-[hydroxy(1-methyl-1H-imidazol-5-yl)[4-[(2-thiazolylthio)methyl]phenyl]methyl]-1-methyl-2(1H)-quinolinone, as a white foam, MS (ESI) m/z:585, 586 (MH+).

Workup

  1. extractionextracted with CH2Cl2/CH3OH
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography over kromasil 60 μm (eluent: CH2Cl2/CH3OH; 90/10)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e7cdb5571fc34a11bd9be9c0fbea1805
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

Loading…