Lithium Hydroxide → HCID 59208459, compound

HRID 2243029Notes

Reaction equation

HRID 2243029 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[N:7]=[C:8]([C:16]2[CH:17]=[N:18][C:19]([NH:22][C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:21]=2)[S:9][C:10]=1[C:11]([O:13]CC)=[O:12])=[O:5])[CH3:2].[OH-].[Li+]>CO>[CH2:1]([NH:3][C:4]([C:6]1[N:7]=[C:8]([C:16]2[CH:17]=[N:18][C:19]([NH:22][C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:21]=2)[S:9][C:10]=1[C:11]([OH:13])=[O:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59208394HCID 59208394, compound

Product 1

HCID 59208459HCID 59208459, compoundYield 66,683.703%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of ethyl 4-ethylcarbamoyl-2-[6-(3-ethyl-ureido)-pyridin-3-yl]-thiazole-5-carboxylate (Example 59, 0.210 mg, 0.538 mM) in methanol (4 mL) was added 2 N lithium hydroxide (2 mL). The reaction mixture was heated to 50° C. overnight, then cooled to room temperature, and concentrated to dryness. Water was added and the pH was adjusted with 2N hydrochloric acid to pH 2. The precipitated solid was filtered and dried under vacuum to afford 0.13 g (66.6%) of the title compound as a solid. NMR: 1.11 (t, 3H), 1.23 (t, 3H), 3.19 (q, 4H), 7.71 (d, 1H), 7.81 (br s, 1H), 8.41 (d, 1H), 9.01 (s, 1H), 9.66 (s, 1H), 9.83 (br s, 1H).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated to dryness
  3. additionWater was added
  4. filtrationThe precipitated solid was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ce359dae5cc14872bcd956e59c5f8641
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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