Water → HCID 59135660, compound

HRID 1960303Notes

Reaction equation

HRID 1960303 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21]1[S:22][C:23]([CH2:26]O)=[CH:24][N:25]=1)[NH:6]2.O1[CH2:32][CH2:31]CC1.S(Cl)(Cl)=O.[OH2:37]>>[C:7]([N:6]1[CH2:32][CH2:31][N:25]([CH2:26][C:23]2[S:22][C:21]([C:5]3[NH:6][C:7]4[C:3]([CH:4]=3)=[C:2]([Cl:1])[CH:10]=[CH:9][C:8]=4[N:11]([CH3:20])[S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])=[N:25][CH:24]=2)[CH2:21][CH2:5]1)(=[O:37])[CH3:3]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 11948702HCID 11948702, compound

Product 1

HCID 59135660HCID 59135660, compoundYield 25%

Procedure

To a mixture of N-{4-chloro-2-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide (0.26 g) and tetrahydrofuran (10 ml) was added thionyl chloride (0.08 ml) at 0° C., and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. A mixture of the obtained residue, 1-acetylpiperazine (0.15 g), triethylamine (0.17 ml) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to basic silica gel column chromatography to give the title compound (0.08 g, yield 25%) as colorless crystals from a fraction eluted with ethyl acetate. melting point 224-225° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additionA mixture of the obtained residue, 1-acetylpiperazine (0.15 g), triethylamine (0.17 ml) and N,N-dimethylformamide (10 ml)
  6. stirringwas stirred at room temperature for 3 hr
  7. additionWater was added to the reaction mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with saturated brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-1ebec4c630cb47e6b2bdcb04cff8ea70
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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