Ethanol → HCID 20094541, compound

HRID 274136Notes

Reaction equation

HRID 274136 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]([CH:16]=[O: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]([CH:16]=[O:17])=[C:13]([Cl:15])[N:14]=1)[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 20094522HCID 20094522, compound

Product 1

HCID 20094541HCID 20094541, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethanol (0.8 ml), ion-exchanged water (0.2 ml), and potassium hydroxide (28 mg) were added to 2-butyl-4-chloro-1-[2-(2-ethoxycarbonylphenyl)-2H-indazol-5-yl]methyl-1H-imidazole-5-carbaldehyde (61 mg, 0.13 mmol) as obtained in Example 1, and the mixture was stirred at room temperature for 2 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 1. The resultant solid was filtered off and washed three times with ion-exchanged water (1 ml). It was then dried in vacuo overnight at 37° C. to give 36 mg of 2-butyl-4-chloro-1-[2-(2-carboxyphenyl)-2H-indazol-5-yl]methyl-1H-imidazole-5-carbaldehyde.

Workup

  1. customas obtained in Example 1
  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. customIt was then dried in vacuo overnight at 37° C.

Sources & evidence

ORD record
ord-7e6a336abe5d47b0990612cfc20a02d5
Source dataset
uspto-grants-1995_02
Patent number
US05387684

Reaction notes

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