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

HRID 245114Notes

Reaction equation

HRID 245114 reaction equation
[CH:1]1([C:6]2[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH3:16])[N:14]=2)[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]([C:19]1[CH:20]=[C:21]([CH:26]=[C:27]([CH3:34])[C:28]=1[NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:22]([NH:24]O)=[NH:23])[CH3:18]>>[CH:1]1([C:6]2[CH:7]=[C:8]([C:9]3[O:11][N:24]=[C:22]([C:21]4[CH:26]=[C:27]([CH3:34])[C:28]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[C:19]([CH2:17][CH3:18])[CH:20]=4)[N:23]=3)[CH:12]=[C:13]([O:15][CH3:16])[N:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 584180372-Cyclopentyl-6-methoxyisonicotinic acidHCID 178436625HCID 178436625, compound

Product 1

HCID 49872261N-{4-[5-(2-Cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenyl}-methanesulfonamideYield 48.4%

Procedure

The title compound (48 mg) is prepared in analogy to Example 11 starting from 2-cyclopentyl-6-methoxy-isonicotinic acid (48 mg, 217 μmol) and 3-ethyl-N-hydroxy-4-methanesulfonylamino-5-methyl-benzamidine (62 mg, 228 mmol); LC-MS**: tR=0.91 min, [M+H]+=457.05; 1H NMR (CDCl3): δ1.35 (t, J=7.5 Hz, 3H), 1.71-1.80 (m, 2H), 1.84-1.95 (m, 4H), 2.06-2.16 (m, 2H), 2.56 (s, 3H), 2.93 (q, J=7.5 Hz, 2H), 3.18 (s, 3H), 3.21-3.30 (m, 1H), 4.02 (s, 3H), 5.88 (s, 1H), 7.31 (s, 1H), 7.51 (s, 1H), 7.97 (s, 1H), 7.99 (s, 1H).

Sources & evidence

ORD record
ord-66c1d3b8b8b04a7a9c4ce0c33c92de0f
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

Loading…