Lithium Hydroxide → HCID 18771641, compound

HRID 479684Notes

Reaction equation

HRID 479684 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][CH:9]=[C:10]([NH:12][C:13](=[O:33])[NH:14][C:15]3[N:20]=[C:19]([CH2:21][N:22]4[CH2:27][CH2:26][CH:25]([C:28]([O:30]CC)=[O:29])[CH2:24][CH2:23]4)[CH:18]=[CH:17][CH:16]=3)[N:11]=2)=[CH:3][CH:2]=1.[Li+].[OH-]>CO.O>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[S:8][CH:9]=[C:10]([NH:12][C:13](=[O:33])[NH:14][C:15]3[N:20]=[C:19]([CH2:21][N:22]4[CH2:23][CH2:24][CH:25]([C:28]([OH:30])=[O:29])[CH2:26][CH2:27]4)[CH:18]=[CH:17][CH:16]=3)[N:11]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 18771796HCID 18771796, compound

Product 1

HCID 18771641HCID 18771641, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

Ethyl 1-{6-[3-(2-(pyridin-4-yl)thiazol-4-yl)ureido]-pyridin-2-ylmethyl}-piperidine-4-carboxylate (55 mg, 0.12 mmol, Example 61) was suspended in MeOH (10 ml) followed by adding LiOH (50 mg, 1.18 mmol) in H2O (1 ml). The resulting mixture was heated at 45° C. for 15 h. After cooling to RT, the solvent was removed. The residue was suspended in H2O (20 mL). The pH was adjusted to 7 using HCl (1N). The resulting mixture was extracted with CHCl3:IpOH (3:1). The organic layer was washed with H2O and brine. After being dried over anhydrous MgSO4, the solvent was removed in vacuo to yield the final compound as light yellow solid. MS m/z: 438.7 (M+H). Calc'd. for C21H22N6O3S-438.51.

Workup

  1. temperatureAfter cooling to RT
  2. customthe solvent was removed
  3. extractionThe resulting mixture was extracted with CHCl3
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialAfter being dried over anhydrous MgSO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5ab6ab39648e4c1b9a41c48ddf899ab0
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

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