Tetrahydrofuran → HCID 136060812, compound

HRID 1851522Notes

Reaction equation

HRID 1851522 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[NH:21][S:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)(=[O:24])=[O:23])[S:5][C:6]=1[C:7]([O:9]CC)=[O:8].[OH-].[Na+].O1CCCC1>CO>[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[NH:21][S:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)(=[O:24])=[O:23])[S:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 136060809HCID 136060809, compound

Product 1

HCID 136060812HCID 136060812, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 4-methyl-2-{7-[(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-5-carboxylate (0.42 g), 8N aqueous sodium hydroxide solution (0.4 mL), tetrahydrofuran (6 mL) and methanol (6 mL) was stirred at 60° C. for 1 hr. The reaction mixture was concentrated, and water was added to the residue. The mixture was acidified with 10% aqueous citric acid solution, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were dissolved in tetrahydrofuran, treated with activated carbon, and concentrated to give the title compound (0.17 g, yield 44%) as yellow crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point>253° C. (decomposition).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. filtrationthe resulting crystals were filtrated
  4. washwashed with water
  5. customdried
  6. dissolutionThe obtained crystals were dissolved in tetrahydrofuran
  7. additiontreated with activated carbon
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d32ab5e37c1c4fcd88dad7f1940b9322
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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