Lithium Hydroxide → 2-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

HRID 2243020Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]([O:20]C)=[O:19])=[CH:16][N:17]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].[Li+].[OH-]>CO>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]([OH:20])=[O:19])=[CH:16][N:17]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

Methyl-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylate (Example 1, 0.185 g, 0.60 mmol) was taken in MeOH (6 mL) and 2N LiOH (1 mL) was added to it. The resulting mixture was stirred at 45° C. for two hours. The solvent was removed and the aqueous was diluted with water and acidified with 1N HCl. The precipitated product was collected by filtration and washed with water and dried (0.17 g). MS (ESP): 293 (M+H+) for C12H12N4O3S; NMR: 1.09 (t, 3H), 3.16-3.22 (m, 2H), 7.60 (d, 1H), 7.81 (t, 1H), 8.26 (dd, 1H), 8.38 (s, 1H), 8.81 (s, 1H), 9.54 (s, 1H), 13.54 (brs, 1H).

Workup

customThe solvent was removed
additionthe aqueous was diluted with water
filtrationThe precipitated product was collected by filtration
washwashed with water
customdried (0.17 g)

Sources & evidence

ORD record: ord-91230c47c05042c08461a258fa31d767
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674801B2

Reaction notes

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