Ethanol → HCID 20094530, compound

HRID 274134Notes

Reaction equation

HRID 274134 reaction equation
C(O)C.[OH-].[K+].[CH2:6]([C:10]1[N:11]([CH2:18][C:19]2[CH:27]=[CH:26][C:25]3[C:21](=[CH:22][N:23]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([O:36]CC)=[O:35])[N:24]=3)[CH:20]=2)[C:12]([CH2:16][OH:17])=[C:13]([Cl:15])[N:14]=1)[CH2:7][CH2:8][CH3:9]>O>[CH2:6]([C:10]1[N:11]([CH2:18][C:19]2[CH:27]=[CH:26][C:25]3[C:21](=[CH:22][N:23]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([OH:36])=[O:35])[N:24]=3)[CH:20]=2)[C:12]([CH2:16][OH:17])=[C:13]([Cl:15])[N:14]=1)[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 20094563HCID 20094563, compound

Product 1

HCID 20094530HCID 20094530, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethanol (1.5 ml), ion-exchanged water (0.3 ml), and potassium hydroxide (42 mg) were added to 2-butyl-4-chloro-1-[2-(2-ethoxycarbonylphenyl)-2H-indazol-5-yl]methyl-5-(hydroxymethyl)-1H-imidazole (116 mg, 0.248 mmol) as obtained in Example 3, and the mixture was stirred at room temperature for 1.5 hours. The mixture was concentrated in an evaporator, and partitioned by ion-exchanged water (2.5 ml) and diethyl ether (5 ml). The water layer was separated and conc. hydrochloric acid was dropwise added thereto to adjust its pH to 2. The resultant solid was filtered off and washed three times with ion-exchanged water (1 ml). The solid was dried in vacuo at 37° C. overnight to give 58 mg of 2-butyl-4-chloro-1-[2-(2-carboxyphenyl)-2H-indazol-5-yl]methyl-5-(hydroxymethyl)-1H-imidazole.

Workup

  1. customas obtained in Example 3
  2. concentrationThe mixture was concentrated in an evaporator
  3. custompartitioned by ion-exchanged water (2.5 ml) and diethyl ether (5 ml)
  4. customThe water layer was separated
  5. additionconc. hydrochloric acid was dropwise added
  6. filtrationThe resultant solid was filtered off
  7. washwashed three times with ion-exchanged water (1 ml)
  8. customThe solid was dried in vacuo at 37° C. overnight

Sources & evidence

ORD record
ord-da717163e9a34bb5b48123a2335a979b
Source dataset
uspto-grants-1995_02
Patent number
US05387684

Reaction notes

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