Dimethylacetamide → HCID 59135792, compound

HRID 1851623Notes

Reaction equation

HRID 1851623 reaction equation
[CH:1]1([CH2:4][N:5]([S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:14]=2[NH:13][C:12]([C:15](=[S:17])[NH2:16])=[CH:11]3)[CH2:3][CH2:2]1.Br[CH:27]([CH:30]=O)[CH:28]=[O:29].CN(C)C(=O)C>O>[CH:1]1([CH2:4][N:5]([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:14]=2[NH:13][C:12]([C:15]2[S:17][C:27]([CH2:28][OH:29])=[CH:30][N:16]=2)=[CH:11]3)[S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:20])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 749452-BromopropanedialHCID 57475961HCID 57475961, compound

Product 1

HCID 59135792HCID 59135792, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-[(cyclopropylmethyl)(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (225 mg), bromomalonaldehyde (182 mg) and N,N-dimethylacetamide (3 mL) was stirred at 90° C. for 1 hr. Water was added and the obtained precipitate was washed with water, and then with hexane. The solid was dissolved in a mixture of tetrahydrofuran (5 mL) and methanol (5 mL), and the mixture was cooled in an ice bath. Sodium borohydride (20 mg) was added and the mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated, and the residue was diluted with a mixture of tetrahydrofuran-ethyl acetate (1:1) and washed with saturated brine and aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtrated, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography and eluted with a mixture of ethyl acetate-hexane. The obtained solid was washed with a mixture of hexane-ether to give the title compound (100 mg, yield 50%) as crystals. melting point 174° C.

Workup

  1. washthe obtained precipitate was washed with water
  2. dissolutionThe solid was dissolved in a mixture of tetrahydrofuran (5 mL) and methanol (5 mL)
  3. temperaturethe mixture was cooled in an ice bath
  4. additionSodium borohydride (20 mg) was added
  5. stirringthe mixture was stirred at room temperature for 3 days
  6. concentrationThe reaction mixture was concentrated
  7. additionthe residue was diluted with a mixture of tetrahydrofuran-ethyl acetate (1:1)
  8. washwashed with saturated brine and aqueous sodium bicarbonate
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. filtrationfiltrated
  11. concentrationthe filtrate was concentrated
  12. washeluted with a mixture of ethyl acetate-hexane
  13. washThe obtained solid was washed with a mixture of hexane-ether

Sources & evidence

ORD record
ord-ef3892f8c77b4dee95d32d54404d04e8
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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