2-(Diethylamino)-6-methylisonicotinic acid → 2-{4-[5-(2-Diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethanol

HRID 2047339Notes

Reaction equation

HRID 2047339 reaction equation
[OH:1][NH:2][C:3](=[NH:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.[CH2:14]([N:16]([CH2:27][CH3:28])[C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([CH3:26])[N:25]=1)[C:20](O)=O)[CH3:15]>>[CH2:27]([N:16]([CH2:14][CH3:15])[C:17]1[CH:18]=[C:19]([C:20]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][OH:12])=[CH:8][CH:9]=3)[N:13]=2)[CH:23]=[C:24]([CH3:26])[N:25]=1)[CH3:28]

Participants

3

Reactant 2

HCID 584180552-(Diethylamino)-6-methylisonicotinic acidHCID 59604233CID 59604233

Product 1

HCID 685786612-{4-[5-(2-Diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethanol

Procedure

The title compound is prepared in analogy to Example 5 starting from N-hydroxy-4-(2-hydroxy-ethyl)-benzamidine and 2-diethylamino-6-methyl-isonicotinic acid; LC-MS: tR=1.07*min; [M+1]+=353.11; 1H NMR (CDCl3): δ 1.25 (t, J=6.8 Hz, 6H), 2.50 (s, 3H), 2.98 (t, J=6.3 Hz, 2H), 3.63 (q, J=7.0 Hz, 4H), 3.95 (q, J=6.0 Hz, 2H), 7.02 (s, 1H), 7.10 (s, 1H), 7.41 (d, J=7.5 Hz, 2H), 8.15 (d, J=7.5 Hz, 2H).

Sources & evidence

ORD record
ord-f4c3a94b6de54bf9a240ae5daa5f5daa
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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