Lithium Hydroxide → 4-[(Dimethylamino)carbonyl]-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

HRID 2243027Notes

Reaction equation

[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[N:6]=[C:7]([C:15]2[CH:16]=[N:17][C:18]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:19][CH:20]=2)[S:8][C:9]=1[C:10]([O:12]CC)=[O:11])=[O:4].[OH-].[Li+]>CO>[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[N:6]=[C:7]([C:15]2[CH:16]=[N:17][C:18]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:19][CH:20]=2)[S:8][C:9]=1[C:10]([OH:12])=[O:11])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of ethyl 4-dimethylcarbamoyl-2-[6-(3-ethyl-ureido)-pyridin-3-yl]-thiazole-5-carboxylate (Example 52, 0.7 g, 1.78 mmol) in methanol (15 mL) was added 2 N lithium hydroxide (8 mL). The mixture was heated to 50° C. overnight. After completion of the reaction, the reaction mixture was concentrated to dryness. Water was added and the pH was adjusted with 2 N hydrochloric acid to pH 2. The precipitated solid was filtered and dried under vacuum to afford 0.2 g (35.48%) of the title compound as a pale brown solid. MS (APCI): 364 (M+H+) for C16H18N4O4S; NMR: δ 1.1 (t, 3H), δ 2.8 (s, 3H), δ 3.07 (s, 3H), δ 7.62 (d, 1H), δ 7.75 (br s, 1H), δ 8.25 (d, 1H), δ 8.82 (s, 1H), δ 9.55 (br s, 1H).

Workup

customAfter completion of the reaction
concentrationthe reaction mixture was concentrated to dryness
additionWater was added
filtrationThe precipitated solid was filtered
customdried under vacuum

Sources & evidence

ORD record: ord-994a09df5dc24cdb88269beb5091dfda
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674801B2

Reaction notes

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