2-Cyclohexyl-6-methoxy-isonicotinic acid → N-{4-[5-(2-Cyclohexyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenyl}-methanesulfonamide

HRID 245115Notes

Reaction equation

HRID 245115 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[C:14]([O:16][CH3:17])[N:15]=2)[C:10]([OH:12])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([C:20]1[CH:21]=[C:22]([CH:27]=[C:28]([CH3:35])[C:29]=1[NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[C:23]([NH:25]O)=[NH:24])[CH3:19]>>[CH:1]1([C:7]2[CH:8]=[C:9]([C:10]3[O:12][N:25]=[C:23]([C:22]4[CH:27]=[C:28]([CH3:35])[C:29]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[C:20]([CH2:18][CH3:19])[CH:21]=4)[N:24]=3)[CH:13]=[C:14]([O:16][CH3:17])[N:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 674911482-Cyclohexyl-6-methoxy-isonicotinic acidHCID 178436625HCID 178436625, compound

Product 1

HCID 49872262N-{4-[5-(2-Cyclohexyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenyl}-methanesulfonamideYield 10.1%

Procedure

The title compound (7 mg) is prepared in analogy to Example 11 starting from 2-cyclohexyl-6-methoxy-isonicotinic acid (40 mg, 147 μmol) and 3-ethyl-N-hydroxy-4-methanesulfonylamino-5-methyl-benzamidine (42 mg, 155 mmol); LC-MS**: tR=0.94 min, [M+H]+=471.02; 1H NMR (CDCl3): δ1.35 (t, J=7.8 Hz, 3H), 1.40-1.70 (m, 5H), 1.77-1.84 (m, 1H), 1.88-1.96 (m, 2H), 2.00-2.08 (m, 2H), 2.56 (s, 3H), 2.71-2.81 (m, 1H), 2.93 (q, J=7.0 Hz, 2H), 3.18 (s, 3H), 4.03 (s, 3H), 5.87 (s, 1H), 7.32 (s, 1H), 7.49 (s, 1H), 7.97 (s, 1H), 7.99 (s, 1H).

Sources & evidence

ORD record
ord-e6e05029ffb242c4ad769beab843a0d2
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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