Tetrahydrofuran → HCID 136060807, compound

HRID 1851440Notes

Reaction equation

HRID 1851440 reaction equation
[C:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][S:13]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(=[O:15])=[O:14])#[N:2].Cl.ON.C([N:26]([CH2:29]C)CC)C.[O:31]1CCCC1>O.CO>[O:31]1[CH:29]=[N:26][C:1]([C:3]2[NH:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][C:6]=3[NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:15])=[N:2]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 57901755HCID 57901755, compound

Product 1

HCID 136060807HCID 136060807, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-(2-cyano-1H-indol-7-yl)thiophene-2-sulfonamide (0.50 g), hydroxyamine hydrochloride (0.17 g), triethylamine (0.83 mL), tetrahydrofuran (2 mL) and methanol (2 mL) was stirred at room temperature overnight. Water was added to the reaction mixture, and the obtained crystals were filtrated, washed with water and dried. A mixture of the obtained crystals and methyl orthoformate (10 mL) was heated under reflux for 4 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography. The title compound (0.18 g, yield 33%) was obtained as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point>185° C. (decomposition).

Workup

  1. filtrationthe obtained crystals were filtrated
  2. washwashed with water
  3. customdried
  4. additionA mixture of the obtained crystals and methyl orthoformate (10 mL)
  5. temperaturewas heated
  6. temperatureunder reflux for 4 hr
  7. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-926696e7e2504b04ad96fbd2b0349d04
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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