Ethanol → HCID 20094536, compound

HRID 274135Notes

Reaction equation

HRID 274135 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](=[C:22]([Br:39])[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](=[C:22]([Br:39])[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 20094534HCID 20094534, compound

Product 1

HCID 20094536HCID 20094536, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethanol (1.2 ml ), ion-exchanged water (0.3 ml ), and potassium hydroxide (28 mg) were added to 2-butyl4-chloro-1-[3-bromo-2- (2-ethoxycarbonylphenyl)-2H-indazol-5-yl]methyl-1 H-imidazole-5-carbaldehyde (101 mg, 0.186 mmol) as obtained in Example 1, and the mixture was stirred at room temperature for one day. 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 5. The resultant solid was filtered off and washed three times with ion-exchanged water (1 ml). The solid was dried in vacuo overnight at 37° C. to give 72 mg of 2-butyl-4-chloro-1-[3-bromo-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. customThe solid was dried in vacuo overnight at 37° C.

Sources & evidence

ORD record
ord-54abfc4d2f234f5ca26b2ded46ba518f
Source dataset
uspto-grants-1995_02
Patent number
US05387684

Reaction notes

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