Acetic Acid → HCID 59135968, compound

HRID 504716Notes

Reaction equation

HRID 504716 reaction equation
[CH2:1]([S:8][C:9]1([CH2:19][NH:20][C:21]([C:23]2[NH:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][C:26]=3[N:32]([CH3:41])[S:33]([C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)(=[O:35])=[O:34])=[O:22])[CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>O>[CH2:1]([S:8][C:9]1([CH2:19][NH:20][C:21]([C:23]2[NH:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][C:26]=3[N:32]([CH3:41])[S:33]([C:36]2[S:37][CH:38]=[CH:39][CH:40]=2)(=[O:35])=[O:34])=[O:22])[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 59135872HCID 59135872, compound

Product 1

HCID 59135968HCID 59135968, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-{[8-(benzylthio)-1,4-dioxaspiro[4.5]dec-8-yl]methyl}-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (1.21 g) and acetic acid (15 mL) was added at 80° C. for 24 hr, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried (MgSO4), and concentrated. The residue was subjected to basic silica gel column chromatography to give the title compound (0.79 g, yield 71%) as a colorless amorphous solid from a fraction eluted with tetrahydrofuran-methanol (1:1, volume ratio). MS: 568 (MH+).

Workup

  1. additionwas added at 80° C. for 24 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6e658a94a4ea40809ccee97c386cd36f
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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