5-(4-Iodophenyl)-3-methyl-1,2,4-oxadiazole → 6-Methyl-4'(3-methyl-[1,2,4]oxadiazol-5-yl)biphenyl-3-carboxylic acid [1,3,4]thiadiazol-2-ylamide

HRID 31455Notes

Reaction equation

HRID 31455 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:4][CH:3]=1.[CH3:14][C:15]1[CH:28]=[CH:27][C:18]([C:19]([NH:21][C:22]2[S:23][CH:24]=[N:25][N:26]=2)=[O:20])=[CH:17][C:16]=1B1OC(C)(C)C(C)(C)O1>CN(C=O)C>[S:23]1[CH:24]=[N:25][N:26]=[C:22]1[NH:21][C:19]([C:18]1[CH:17]=[C:16]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:12][N:11]=[C:10]([CH3:13])[N:9]=3)=[CH:4][CH:3]=2)[C:15]([CH3:14])=[CH:28][CH:27]=1)=[O:20]

Participants

4

Reactant 2

HCID 197031165-(4-Iodophenyl)-3-methyl-1,2,4-oxadiazole2×HCID 586565324-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-([1,3,4]thiadiazol-2-yl)-benzamide

Product 1

HCID 102490166-Methyl-4'(3-methyl-[1,2,4]oxadiazol-5-yl)biphenyl-3-carboxylic acid [1,3,4]thiadiazol-2-ylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Example 27 was prepared using 5-(4-iodophenyl)-3-methyl-[1,2,4]oxadiazole (Intermediate 12) and 4-methyl-3-(4,4,5,5, -tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-([1,3,4]thiadiazol-2-yl)-benzamide (Intermediate 23) using DMF as the solvent.

Workup

  1. customExample 27 was prepared

Sources & evidence

ORD record
ord-7cfa817061d94cf982197f31a48d9bbf
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Reaction notes

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