HCID 68381586, compound → HCID 67118499, compound

HRID 1188976Notes

Reaction equation

HRID 1188976 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][O:8][C:9]1[CH:10]=[C:11]([O:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:19][CH:20]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:21][N:22]=1)=[CH:14]2>O1CCCC1.C(O)C.[OH-].[Na+]>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][O:8][C:9]1[CH:10]=[C:11]([O:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:37])=[O:38])=[CH:32][CH:31]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:19][CH:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:21][N:22]=1)=[CH:14]2

Participants

5

Reactant 1

HCID 68381586HCID 68381586, compound

Product 1

HCID 67118499HCID 67118499, compoundYield 17.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl (2-{7-[(1-methyl-1H-imidazol-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (1 g) was dissolved in a mixed solvent of tetrahydrofuran (10 mL)-ethanol (10 mL), 1M aqueous sodium hydroxide solution (5 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction solution was concentrated under reduced pressure. Water was added to the residue, and the mixture was neutralized with 1M hydrochloric acid. The mixture was washed with ethyl acetate, and the aqueous layer was concentrated under reduced pressure. Ethanol was added to the residue, and the insoluble substance was filtered off. The filtrate was concentrated, and the obtained yellow solid was recrystallized from ethanol to give the title compound (170 mg) as yellow crystals. MS 541 (MH+).

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. washThe mixture was washed with ethyl acetate
  5. concentrationthe aqueous layer was concentrated under reduced pressure
  6. additionEthanol was added to the residue
  7. filtrationthe insoluble substance was filtered off
  8. concentrationThe filtrate was concentrated
  9. customthe obtained yellow solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-b64de957e851486dbeabd48105a19c4c
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

Loading…