Water → HCID 178513363, compound

HRID 1020198Notes

Reaction equation

HRID 1020198 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([S:18]([C:21]2[S:25][C:24]([C:26]#[N:27])=[CH:23][CH:22]=2)(=O)=[O:19])[CH2:13][CH2:12]3)=[CH:5][CH:4]=1.Cl.[NH2:31][OH:32].C(N(CC)CC)C.[OH2:40]>O1CCCC1.CO>[OH:32][NH:31][C:26]([C:24]1[S:25][C:21]([S:18]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:28])([F:1])[F:29])=[CH:4][CH:5]=4)=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)(=[O:19])=[O:40])=[CH:22][CH:23]=1)=[NH:27]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 67017209HCID 67017209, compound

Product 1

HCID 178513363HCID 178513363, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

150 mg 5-[5-(4-Trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-thiophene-2-carbonitrile were dissolved in a mixture of 8 ml tetrahydrofuran and 8 ml methanol. 600 mg hydroxylamine hydrochloride were added followed by the addition of 1.20 ml triethylamine. The reaction mixture was stirred at room temperature for four hours. The mixture was poured on 100 ml water and extracted five times with portions of 50 ml ethylacetate. The combined organic extracts were washed with 100 ml brine, dried over MgSO4 and the solvent was evaporated in vacuo to obtain 163 mg N-Hydroxy-5-[5-(4-trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-thiophene-2-carboxamidine. This material was used without further purification.

Workup

  1. extractionextracted five times with portions of 50 ml ethylacetate
  2. washThe combined organic extracts were washed with 100 ml brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-c16752eac3b446ca8f559bb7c2532d17
Source dataset
uspto-grants-2014_05
Patent number
US08716317B2

Reaction notes

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