3-Iodobenzoic acid → 2-hydroxy-N-[4-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]-2-[3-oxo-4-(p-tolyl)thiomorpholin-2-yl]acetamide

HRID 876616Notes

Reaction equation

HRID 876616 reaction equation
[OH:1][CH:2]([CH:6]1[S:11][CH2:10][CH2:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:7]1=[O:19])[C:3]([OH:5])=O.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[NH:28][O:29][C:30](=[O:32])[N:31]=2)=[CH:23][CH:22]=1.IC1C=C(C=CC=1)C(O)=O.FC1(F)CCNCC1>>[OH:1][CH:2]([CH:6]1[S:11][CH2:10][CH2:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:7]1=[O:19])[C:3]([NH:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[NH:31][C:30](=[O:32])[O:29][N:28]=2)=[CH:25][CH:26]=1)=[O:5]

Participants

5

Reactant 4

HCID 120603-Iodobenzoic acidHCID 27583524,4-DifluoropiperidineHCID 672221082-Hydroxy-2-[3-oxo-4-(p-tolyl)thiomorpholin-2-yl]acetic acidHCID 178507458HCID 178507458, compound

Product 1

HCID 1363377912-hydroxy-N-[4-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]-2-[3-oxo-4-(p-tolyl)thiomorpholin-2-yl]acetamideYield 60.4%

Procedure

According to the Step 77-1 in synthetic method for EXAMPLE 77, compound 112-2 (0.55 g) and 3-(4-aminophenyl)-1,2,4-oxadiazol-5(2H)-one (0.52 g) were used instead of 3-iodobenzoic acid and 4,4-difluoropiperidine to obtain compound 112-3 (0.52 g) as a pale yellow amorphous solid.

Sources & evidence

ORD record
ord-5ec943429378488ab6f5fa5e8d2a9d94
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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