Sodium Hydroxide → HCID 89767207, compound

HRID 1752515Notes

Reaction equation

HRID 1752515 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[S:24][CH:25]=[C:26]([C:28]([O:30]C)=[O:29])[N:27]=2)[CH2:18][CH2:17]1)=[O:13].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[S:24][CH:25]=[C:26]([C:28]([OH:30])=[O:29])[N:27]=2)[CH2:18][CH2:17]1)=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89767420HCID 89767420, compound

Product 1

HCID 89767207HCID 89767207, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 7 (1.85 mmoles) in MeOH (10 mL) aqueous 1M NaOH (3.7 mL) was added. The solution was refluxed overnight then the organic solvent was removed under vacuum, the residue was diluted with H2O and the pH was adjusted to 5 by adding 1M HCl. The mixture was kept at 4° C. overnight then the resulting solid was filtered, washed with fresh water and dried under vacuum to give 2-{[4-({[(5-Methoxy-1H-indazol-3-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}-1,3-thiazole-4-carboxylic acid 8 (43% yield).

Workup

  1. temperatureThe solution was refluxed overnight
  2. customthe organic solvent was removed under vacuum
  3. additionthe residue was diluted with H2O
  4. additionby adding 1M HCl
  5. filtrationthe resulting solid was filtered
  6. washwashed with fresh water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-11444f69f27d4c0ba75d38de67be0217
Source dataset
uspto-grants-2015_10
Patent number
US09163013B2

Reaction notes

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