Dimethylacetamide → HCID 59135949, compound

HRID 1851624Notes

Reaction equation

HRID 1851624 reaction equation
[CH:1]([N:4]([S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14](=[S:16])[NH2:15])=[CH:10]2)([CH3:3])[CH3:2].Br[CH:26]([CH:29]=O)[CH:27]=[O:28].CN(C)C(=O)C>O>[OH:28][CH2:27][C:26]1[S:16][C:14]([C:11]2[NH:12][C:13]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]([CH:1]([CH3:3])[CH3:2])[S:17]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:19])=[N:15][CH:29]=1

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 749452-BromopropanedialHCID 57475963HCID 57475963, compound

Product 1

HCID 59135949HCID 59135949, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-[isopropyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (123 mg), bromomalonaldehyde (103 mg) and N,N-dimethylacetamide (3 mL) was stirred at 90° C. for 2 hr. To the reaction mixture was added water, and the obtained solid was washed with water, and then with hexane. To a mixture of the solid, tetrahydrofuran (5 mL) and methanol (5 mL) was added sodium borohydride (15 mg), and the mixture was stirred at room temperature for 14 hr. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with aqueous sodium bicarbonate and saturated brine, and the ethyl acetate layer was dried over magnesium sulfate, and filtrated. The filtrate was concentrated. The residue was subjected to silica gel column chromatography, and eluted with a mixture of ethyl acetate-hexane (2:1) to give the title compound (124 mg, yield 88%) as crystals. melting point 209° C.

Workup

  1. washthe obtained solid was washed with water
  2. additionTo a mixture of the solid, tetrahydrofuran (5 mL) and methanol (5 mL)
  3. additionwas added sodium borohydride (15 mg)
  4. stirringthe mixture was stirred at room temperature for 14 hr
  5. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  6. additionwas added to the residue
  7. washThe mixture was washed with aqueous sodium bicarbonate and saturated brine
  8. dry with materialthe ethyl acetate layer was dried over magnesium sulfate
  9. filtrationfiltrated
  10. concentrationThe filtrate was concentrated
  11. washeluted with a mixture of ethyl acetate-hexane (2:1)

Sources & evidence

ORD record
ord-c5fab56658004c02b43f2cccbdb2d564
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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