Sodium Hydroxide → 4-[5-(2-Diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid

HRID 2047336Notes

Reaction equation

HRID 2047336 reaction equation
C([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[NH:14])[NH:12][OH:13])=[CH:7][CH:6]=1)C.[CH2:16]([N:18]([CH2:29][CH3:30])[C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([CH3:28])[N:27]=1)[C:22](O)=O)[CH3:17].[OH-].[Na+]>C1COCC1>[CH2:29]([N:18]([CH2:16][CH3:17])[C:19]1[CH:20]=[C:21]([C:22]2[O:13][N:12]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:3])=[O:15])=[CH:10][CH:9]=3)[N:14]=2)[CH:25]=[C:26]([CH3:28])[N:27]=1)[CH3:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 584180552-(Diethylamino)-6-methylisonicotinic acidHCID 178468924HCID 178468924, compound

Product 1

HCID 685785144-[5-(2-Diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared in analogy to Example 8 starting from 4-(N-hydroxycarbamimidoyl)-benzoic acid ethyl ester and 2-diethylamino-6-methyl-isonicotinic acid except that in the final step, the ethyl ester is cleaved under basic conditions (3 N aq. NaOH in THF); LC-MS: tR=0.77 min; [M+1]+=353.09; 1H NMR (D6-DMSO): δ 1.16 (t, J=6.8 Hz, 6H), 2.43 (s, 3H), 3.58 (q, J=6.5 Hz, 4H), 7.00 (s, 1H), 7.07 (s, 1H), 8.00 (d, J=8.0 Hz, 2H), 8.04 (d, J=8.0 Hz, 2H).

Sources & evidence

ORD record
ord-dc33851f83ee4cf5863ab3bc167f7599
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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