Dimethylacetamide → HCID 57475966, compound

HRID 1851626Notes

Reaction equation

HRID 1851626 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.[BH4-].[Na+]>O1CCCC1.CO.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

8

Reactant 4

HCID 31374DimethylacetamideHCID 749452-BromopropanedialHCID 4311764Sodium borohydrideHCID 57475962HCID 57475962, compound

Product 1

HCID 57475966HCID 57475966, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

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. To the reaction mixture was added water, and the obtained precipitate was dissolved in tetrahydrofuran (30 mL) and methanol (30 mL). After cooling in 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 a mixture of ethyl acetate-tetrahydrofuran and washed successively with aqueous sodium bicarbonate and saturated brine. The organic layer was dried over magnesium sulfate and filtrated. The filtrate was concentrated, subjected to silica gel column chromatography, and eluted with an ethyl acetate-hexane (2:1) mixture to give the title compound (800 mg, yield 17%) as a solid.

Workup

  1. temperatureAfter cooling in an ice bath
  2. stirringthe mixture was stirred at room temperature for 16 hr
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with a mixture of ethyl acetate-tetrahydrofuran
  5. washwashed successively with aqueous sodium bicarbonate and saturated brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltrated
  8. concentrationThe filtrate was concentrated
  9. washeluted with an ethyl acetate-hexane (2:1) mixture

Sources & evidence

ORD record
ord-8d2d7e5f49e541e8846c8e1704901be8
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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