Methylparaben → HCID 57901656, compound

HRID 1851627Notes

Reaction equation

HRID 1851627 reaction equation
[CH2:1]([N:3]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][C:23]([CH2:26][OH:27])=[CH:24][N:25]=1)=[CH:17]2)[S:4]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)(=[O:6])=[O:5])[CH3:2].O[C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH2:1]([N:3]([S:4]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:6])[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][C:23]([CH2:26][O:27][C:29]3[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=3)=[CH:24][N:25]=1)=[CH:17]2)[CH3:2]

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 57475966HCID 57475966, compound

Product 1

HCID 57901656HCID 57901656, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-ethyl-N-{2-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide (420 mg) and methyl 4-hydroxybenzoate (153 mg) were dissolved in tetrahydrofuran (10 mL), and tri-tert-butylphosphine (263 mg) and 1,1′-(azodicarbonyl)dipiperidine (328 mg) were added. The reaction mixture was stirred at room temperature for 30 min. The reaction mixture was filtrated and the filtrate was concentrated. The residue was subjected to silica gel column chromatography and eluted with a mixture of ethyl acetate-hexane (1:1) to give the title compound (200 mg, yield 36%) as pale-yellow crystals. melting point 191° C.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated
  3. washeluted with a mixture of ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-14328460c7254e3aa681af4ae848b23f
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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