Tetrahydrofuran → HCID 136060827, compound

HRID 1851529Notes

Reaction equation

HRID 1851529 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]=[C:22]([C:24](OCC)=[O:25])[N:23]=1)=[CH:15]2)(=[O:8])=[O:7].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C(O)C>[OH:25][CH2:24][C:22]1[N:23]=[C:19]([C:16]2[NH:17][C:18]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][C:10]=3[NH:9][S:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)(=[O:8])=[O:7])[S:20][CH:21]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 136060800HCID 136060800, compound

Product 1

HCID 136060827HCID 136060827, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of ethyl 2-{7-[(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-4-carboxylate (0.35 g) and tetrahydrofuran (15 mL) was added lithium aluminum hydride (0.11 g) at 0° C., and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added ethanol (5 mL) and then saturated aqueous ammonium chloride solution (5 mL) was added. The resulting inorganic salt was removed by filtration, and the filtrate was concentrated. The obtained crystals were dissolved in tetrahydrofuran, treated with activated carbon, and concentrated. Ethyl acetate was added to the obtained residue, and the resulting crystals were collected by filtration and dried to give the title compound (0.10 g, yield 32%) as yellow crystals. melting point>233° C. (decomposition).

Workup

  1. customThe resulting inorganic salt was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe obtained crystals were dissolved in tetrahydrofuran
  4. additiontreated with activated carbon
  5. concentrationconcentrated
  6. additionEthyl acetate was added to the obtained residue
  7. filtrationthe resulting crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-5fdca70c29064b7f8b62028616f875b9
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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