1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → Indomethacin

HRID 1472624Notes

Reaction equation

HRID 1472624 reaction equation
C[C:2]1([CH3:11])[N:7]([O])[C:6](C)(C)[CH2:5][CH2:4][CH2:3]1.[CH3:12][C:13]1[N:21]([C:22]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)=[O:23])[C:20]2[CH:19]=[CH:18][C:17]([O:31][CH3:32])=[CH:16][C:15]=2[C:14]=1[CH2:33][C:34]([OH:36])=[O:35].[CH3:37][C:38]1([CH3:48])[N:43]([OH:44])[C:42]([CH3:46])([CH3:45])[CH2:41][CH:40]([OH:47])[CH2:39]1.C(OC1C(=CC=CC=1)C(Cl)=O)(=O)C>>[CH2:3]1[CH2:2][CH2:11][CH:6]([N:7]=[C:22]=[N:21][CH:20]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:5][CH2:4]1.[CH3:37][C:38]1([CH3:48])[N:43]([OH:44])[C:42]([CH3:46])([CH3:45])[CH2:41][CH:40]([OH:47])[CH2:39]1.[CH3:12][C:13]1[N:21]([C:22]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)=[O:23])[C:20]2[CH:19]=[CH:18][C:17]([O:31][CH3:32])=[CH:16][C:15]=2[C:14]=1[CH2:33][C:34]([OH:36])=[O:35]

Participants

6

Reactant 3

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 796682-Acetoxybenzoyl chlorideHCID 178424955HCID 178424955, compound

Product 3

HCID 3715IndomethacinHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 10868Dicyclohexylcarbodiimide

Procedure

Scheme 1 below depicts the chemical synthesis of the ASA and indomethacin-nitroxide conjugates (1) and (2). Condensation of 4-hydroxy-TEMPO with acetylsalicyloyl chloride gave (1) in 48% yield and DCC-mediated coupling of 4-hydroxy-TEMPO with indomethacin gave (2) in 84% yield. The NMR spectroscopy, mass spectrometry and elemental analysis (set forth above) supported the structure of both 1 and 2.

Sources & evidence

ORD record
ord-5febfb947bc14fd28feb5be945595f22
Source dataset
uspto-grants-2015_04
Patent number
US09012647B2

Reaction notes

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