Lithium Hydroxide → HCID 59208514, compound

HRID 2243030Notes

Reaction equation

HRID 2243030 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][CH2:19][CH2:20][CH3:21])[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][CH2:19][CH2:20][CH3:21])[N:16]=2)=[CH:8][CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59208496HCID 59208496, compound

Product 1

HCID 59208514HCID 59208514, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of ethyl 2-[6-(3-ethyl-ureido)-pyridin-3-yl]-4-propylcarbamoyl-thiazole-5-carboxylate (Example 62, 0.33 g, 0.8 mM) in methanol (15 mL) was added 2 N lithium hydroxide (4 mL). The mixture was heated to 50° C. overnight, then concentrated to dryness. 2N hydrochloric acid was added to the concentrate, and the precipitated solid was filtered and dried under vacuum to afford 0.259 g (72%) of the title compound as solid. NMR: 0.92 (t, 3H), 1.10 (t, 3H), 1.63 (m, 2H), 3.20 (q, 2H), 3.36 (q, 2H), 7.67 (d, 1H), 7.68 (br s, 1H), 8.39 (dd, 1H), 9.02 (s, 1H), 9.62 (br s, 1H), 9.78 (br s, 1H).

Workup

  1. concentrationconcentrated to dryness
  2. addition2N hydrochloric acid was added to the concentrate
  3. filtrationthe precipitated solid was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4b79de66fda246ce875d0b38a26b13ca
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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