Hydrochloric Acid → 2-[1-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)yl)phenyl]-1-methylethyl]-4-phenyl-5-thiazoleacetic acid

HRID 1072479Notes

Reaction equation

HRID 1072479 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][C:6]1[S:10][C:9]([C:11]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([N:21]3[C:26](=[O:27])[NH:25][C:24](=[O:28])[CH:23]=[N:22]3)=[CH:16][C:15]=2[Cl:29])([CH3:13])[CH3:12])=[N:8][C:7]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)C.[OH-].[Na+].Cl.CCOC(C)=O>CO.C1COCC1>[Cl:20][C:19]1[CH:18]=[C:17]([N:21]2[C:26](=[O:27])[NH:25][C:24](=[O:28])[CH:23]=[N:22]2)[CH:16]=[C:15]([Cl:29])[C:14]=1[C:11]([C:9]1[S:10][C:6]([CH2:5][C:4]([OH:36])=[O:3])=[C:7]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:8]=1)([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 9828866ethyl-2-[1-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl]phenyl]-1-methylethyl]-4-phenyl-5-thiazoleacetate

Product 1

HCID 158708342-[1-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)yl)phenyl]-1-methylethyl]-4-phenyl-5-thiazoleacetic acidYield 84.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate (9) (0.00183 mole) and NaOH 1N (0.0055 mole) in CH3OH (25 ml) and THF (25 ml) was stirred overnight at RT. The reaction mixture was acidified with 1N HCl (8 ml) and the resulting product was taken up into EtOAc. The organic layer was washed with brine, dried, filtered and the solvent was evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off, washed with DIPE, and dried, yielding 0.8 g (79%) of 2-[1-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)yl)phenyl]-1-methylethyl]-4-phenyl-5-thiazoleacetic acid (intermediate 10).

Workup

  1. washThe organic layer was washed with brine
  2. customdried
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was crystallized from CH3CN
  6. filtrationThe precipitate was filtered off
  7. washwashed with DIPE
  8. customdried

Sources & evidence

ORD record
ord-64ad69748b0a4f4bbe279672e67e234e
Source dataset
uspto-grants-2005_06
Patent number
US06911444B2

Reaction notes

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