4-Propylbenzoic acid → 5-(4-Propylphenyl)-3-(quinolin-5-yl)-1,2,4-oxadiazole

HRID 710478Notes

Reaction equation

HRID 710478 reaction equation
[OH:1][NH:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[NH:4].ONC(C1C2C=CNC=2C=CC=1)=N.[CH2:28]([C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=O)=[CH:33][CH:32]=1)[CH2:29][CH3:30].C(C1C=CC(C(O)=O)=CN=1)CC>>[CH2:28]([C:31]1[CH:39]=[CH:38][C:34]([C:35]2[O:1][N:2]=[C:3]([C:5]3[CH:14]=[CH:13][CH:12]=[C:11]4[C:6]=3[CH:7]=[CH:8][CH:9]=[N:10]4)[N:4]=2)=[CH:33][CH:32]=1)[CH2:29][CH3:30]

Participants

5

Reactant 4

HCID 1376014-Propylbenzoic acidHCID 190793426-Propylnicotinic acidHCID 178513276HCID 178513276, compoundHCID 178513279HCID 178513279, compound

Product 1

HCID 667269365-(4-Propylphenyl)-3-(quinolin-5-yl)-1,2,4-oxadiazoleYield 36%

Procedure

When the product of Step B was substituted for N-hydroxy-1H-indole-4-carboximidamide and 4-propylbenzoic acid was substituted for 6-propylnicotinic acid in Example 66, Step C, the similar process afforded the title compound in 36% yield, as creamy solid. 1H-NMR (CDCl3) 0.97 (tr, 3H, J=9 Hz); 1.7 (m, 2H); 2.69 (tr, 2H, J=9 Hz); 7.38 (d, 2H, J=9 Hz); 7.53 (d, 0.5H, J=6 Hz); 7.56 (d, 0.5H, J=6 Hz); 7.8-7.86 (m, 1H); 8.17 (d, 2H, J=9 Hz); 8.45 (m, 1H); 8.9 (dd, 1H, j=3, 6 Hz); 9.4 (d, 1H, J=9 Hz).

Sources & evidence

ORD record
ord-4a2bfb4a176c44e7911f24b6267e31c5
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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