Lithium Hydroxide → 2-[6-(3-Ethyl-ureido)-pyridin-3-yl]-4-isopropylcarbamoyl-thiazole-5-carboxylic acid

HRID 2243032Notes

Reaction equation

[CH2:1]([NH:3][C:4](=[O:28])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:23]([O:25]CC)=[O:24])=[C:15]([C:17](=[O:22])[NH:18][CH:19]([CH3:21])[CH3:20])[N:16]=2)=[CH:8][CH:7]=1)[CH3:2].[OH-].[Li+]>CO>[CH2:1]([NH:3][C:4](=[O:28])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:23]([OH:25])=[O:24])=[C:15]([C:17](=[O:22])[NH:18][CH:19]([CH3:21])[CH3:20])[N:16]=2)=[CH:8][CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of ethyl 2-[6-(3-ethyl-ureido)-pyridin-3-yl]-4-isopropylcarbamoyl-thiazole-5-carboxylate (Example 65, 0.195 g, 0.48 mmol) in methanol (7 mL) was added 2 N lithium hydroxide (2 mL). The mixture was heated to 50° C. overnight, then concentrated to dryness water was added and the pH was adjusted to pH 2 with 2N hydrochloric acid. The precipitated solid was filtered and dried under vacuum to afford 0.15 g (76.2%) of the title compound as a solid. NMR: 1.11 (t, 3H), 1.28 (d, 6H), 3.22 (q, 2H), 4.20 (m, 1H), 7.62 (d, 1H), 7.7 (r bs, 1H), δ 8.42 (dd, 1H), 8.57 (d, 1H), δ 9.03 (s, 1H).

Workup

concentrationconcentrated to dryness water
additionwas added
filtrationThe precipitated solid was filtered
customdried under vacuum

Sources & evidence

ORD record: ord-741ea68a51944cc384f69106dec4e66b
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674801B2

Reaction notes

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