Indomethacin → HCID 86678236, compound

HRID 1504751Notes

Reaction equation

HRID 1504751 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][S:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[CH3:16][C:17]1[N:25]([C:26]([C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[O:27])[C:24]2[CH:23]=[CH:22][C:21]([O:35][CH3:36])=[CH:20][C:19]=2[C:18]=1[CH2:37][C:38](O)=[O:39].CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([C:26]([N:25]2[C:24]3[C:19](=[CH:20][C:21]([O:35][CH3:36])=[CH:22][CH:23]=3)[C:18]([CH2:37][C:38]([NH:1][CH2:2][CH2:3][S:4][S:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:39])=[C:17]2[CH3:16])=[O:27])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 3715IndomethacinHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22245556tert-butyl N-(2-((2-aminoethyl)disulfanyl)ethyl)carbamate

Product 1

HCID 86678236HCID 86678236, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-(2-(2-aminoethyl)disulfanyl)ethylcarbamate (150 mg, 0.595 mmol) was taken up in CH2C22 (10 mL) along with indomethacin (213 mg, 0.595 mmol) and EDCI (125 mg, 0.65 mmol). The resulting reaction mixture was stirred at room temperature for 18 h and diluted with CH2Cl2. The organic layer was washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by chromatography (CH2Cl2) to afford 312 mg of tert-butyl 2-(2-(2-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetamido)ethyl)disulfanyl)ethylcarbamate (89% yield).

Workup

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with saturated aqueous NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-966794dd17414aa2ba94d4f2a83ce2d0
Source dataset
uspto-grants-2015_12
Patent number
US09216224B2

Reaction notes

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