Dimethylacetamide → HCID 57475966, compound

HRID 1994680Notes

Reaction equation

HRID 1994680 reaction equation
[CH2:1]([N:3]([S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13](=[S:15])[NH2:14])=[CH:9]2)[CH3:2].Br[CH:25]([CH:28]=O)[CH:26]=[O:27].CN(C)C(=O)C>O>[CH2:1]([N:3]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:15][C:25]([CH2:26][OH:27])=[CH:28][N:14]=1)=[CH:9]2)[S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:17])=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 749452-BromopropanedialHCID 57475962HCID 57475962, compound

Product 1

HCID 57475966HCID 57475966, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 7-[ethyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (4.10 g), bromomalonaldehyde (3.55 g) and N,N-dimethylacetamide (30 ml) was stirred at 95° C. for 1.5 hr. Water was added to the reaction mixture, and the obtained precipitate was collected by filtration and dissolved in tetrahydrofuran (30 ml) and methanol (30 ml). After cooling with an ice bath, sodium borohydride (508 mg) was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated, and diluted with ethyl acetate-tetrahydrofuran mixture. The organic layer was washed successively with aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (2:1) mixture to give the title compound (800 mg, yield 17%) as a solid.

Workup

  1. filtrationthe obtained precipitate was collected by filtration
  2. dissolutiondissolved in tetrahydrofuran (30 ml)
  3. temperatureAfter cooling with an ice bath
  4. additionsodium borohydride (508 mg) was added
  5. stirringthe mixture was stirred at room temperature for 16 hr
  6. concentrationThe reaction mixture was concentrated
  7. additiondiluted with ethyl acetate-tetrahydrofuran mixture
  8. washThe organic layer was washed successively with aqueous sodium bicarbonate and saturated brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltrated
  11. concentrationthe filtrate was concentrated
  12. washeluted with ethyl acetate-hexane (2:1) mixture

Sources & evidence

ORD record
ord-5550301239074131b506f704bc92befb
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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