Indomethacin → HCID 67427091, compound

HRID 1504748Notes

Reaction equation

HRID 1504748 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[CH3:15][C:16]1[N:24]([C:25]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[O:26])[C:23]2[CH:22]=[CH:21][C:20]([O:34][CH3:35])=[CH:19][C:18]=2[C:17]=1[CH2:36][C:37](O)=[O:38].CCN=C=NCCCN(C)C>CC#N.CCOC(C)=O>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:25]([N:24]2[C:23]3[C:18](=[CH:19][C:20]([O:34][CH3:35])=[CH:21][CH:22]=3)[C:17]([CH2:36][C:37]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:38])=[C:16]2[CH3:15])=[O:26])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 3715IndomethacinHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 12106198tert-Butyl [2-(2-aminoethoxy)ethyl]carbamate

Product 1

HCID 67427091HCID 67427091, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (150 mg, 0.735 mmol) was then taken up in CH3CN (10 mL) along with indomethacin (263 mg, 0.735 mmol) and EDCI (155 mg, 0.81 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc (20 mL), washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford 310 mg of tert-butyl 2-(2-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetamido)ethoxy)ethylcarbamate (78%).

Workup

  1. customThe resulting reaction mixture
  2. washwashed 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 silica gel chromatography (9:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-e3a01a9193fe4e6ba5c9ca4521cffef2
Source dataset
uspto-grants-2015_12
Patent number
US09216224B2

Reaction notes

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