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

HRID 2243020
Notes
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Reaction equation

HRID 2243020 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59208451Methyl 2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 251261342-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customThe solvent was removed
  2. additionthe aqueous was diluted with water
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with water
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes