5-(3-Chloro-4-propoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazole → HCID 136359946, compound

HRID 717723Notes

Reaction equation

HRID 717723 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([O:25][CH2:26][CH2:27][CH3:28])=[C:21]([CH:24]=3)[C:22]#[N:23])[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8]C(C)C.ClC1C=C(C2ON=C(C3C=CC(OC(C)C)=C(I)C=3)N=2)C=CC=1OCCC>>[OH:8][C:7]1[CH:6]=[CH:5][C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([O:25][CH2:26][CH2:27][CH3:28])=[C:21]([CH:24]=3)[C:22]#[N:23])[O:14][N:13]=2)=[CH:3][C:2]=1[I:1]

Participants

3

Reactant 2

HCID 666149435-(3-Chloro-4-propoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazoleHCID 66615155HCID 66615155, compound

Product 1

HCID 136359946HCID 136359946, compoundYield 74%

Procedure

When the product of Step B was substituted for 5-(3-chloro-4-propoxyphenyl)-3-(3-iodo-4-isopropoxyphenyl)-1,2,4-oxadiazole in Example 36, Step C, the similar procedure afforded the title compound in 74% yield, as creamy solid. 1H NMR (CDCl3) 8.46 (d, 1H, J=1.95 Hz); 8.4 (d, 1H, J=2.13 Hz); 8.31 (dd, 1H, J=8.88, 2.19 Hz); 8.02 (dd, 1H, J=8.49, 1.68 Hz); 7.1 (d, 1H, J=8.94 Hz); 7.09 (d, 1H, J=8.49 Hz); 5.64 (bs, 1H); 4.12 (t, 2H, J=6.48 Hz); 2.02-1.86 (m, 2H); 1.1 (t, 3H, J=7.38 Hz).

Sources & evidence

ORD record
ord-e82af8d361b54ae5aefa31e11f3c9744
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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