Sulfathiazole → Succinylsulfathiazole

HRID 537662Notes

Reaction equation

HRID 537662 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([S:15]([NH:18][C:19]2[S:23][CH:22]=[CH:21][N:20]=2)(=[O:17])=[O:16])[CH:9]=1.C(N(CC)CC)C>O1CCCC1>[CH:12]1[C:13]([NH:14][C:1]([CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:7])=[CH:8][CH:9]=[C:10]([S:15]([NH:18][C:19]2[S:23][CH:22]=[CH:21][N:20]=2)(=[O:17])=[O:16])[CH:11]=1

Participants

5

Reactant 3

HCID 5340SulfathiazoleHCID 7922Succinic anhydrideHCID 8471Triethylamine

Product 1

HCID 5315SuccinylsulfathiazoleYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 27j was synthesized by the method outlined in FIG. 1. Briefly, Compound 27j was synthesized by first complexing succinic anhydride with sulfathiazole by reacting these compounds at room temperature for 6 hours in tetrahydrofuran (THF) in the presence of triethylamine (TEA) to produce succinylsulfathiazole as a white solid (67% yield). The succinylsulfathiazole was then reacted for 2 hours at room temperature with O—(N-succinimidyl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TSTU) in dichloromethane in the presence of TEA to produce the corresponding succinimidyl ester, which was reacted with 1-(4-aminobutyl)-2-{1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl}acetamide in dichloromethane in the presence of TEA at room temperature for 16 hours to produce Compound 27j as a yellow gummy mass (45% yield). Compound 27j was characterized by NMR, two-dimensional NMR, and mass spectroscopy.

Workup

  1. customCompound 27j was synthesized by the method
  2. customat room temperature
  3. customfor 6 hours

Sources & evidence

ORD record
ord-8fd6deb09784415188ca734f94fbc50f
Source dataset
uspto-grants-2014_10
Patent number
US08865130B2

Reaction notes

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