Ethanol → HCID 20094553, compound

HRID 274133Notes

Reaction equation

HRID 274133 reaction equation
C(O)C.[OH-].[K+].[Br:6][C:7]1[N:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([O:37]CC)=[O:36])[N:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([CH2:16][N:17]1[C:21]([CH2:22][OH:23])=[C:20]([Cl:24])[N:19]=[C:18]1[CH2:25][CH2:26][CH2:27][CH3:28])[CH:12]=[CH:11]2>O>[Br:6][C:7]1[N:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([OH:37])=[O:36])[N:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([CH2:16][N:17]1[C:21]([CH2:22][OH:23])=[C:20]([Cl:24])[N:19]=[C:18]1[CH2:25][CH2:26][CH2:27][CH3:28])[CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 20094552HCID 20094552, compound

Product 1

HCID 20094553HCID 20094553, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethanol (1.2 ml), ion-exchanged water (0.3 ml), and potassium hydroxide (45 mg) were added to 1-[3-bromo-2-(2-ethoxycarbonylphenyl)-2H-indazol-5-yl]methyl-2-butyl-4-chloro-5-(hydroxymethyl)-1H-imidazole (106 mg, 0.205 mmol) as obtained in Example 2, 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 5-6. The resultant solid was filtered off and washed twice with ion-exchanged water (1 ml). One drop of conc. hydrochloric acid was added to the filtrate to precipitate solid, which was filtered off, washed with water, and combined with the previously-obtained solid. They were dried in vacuo at 37° C. for two days to give 56 mg of 1-[3-bromo-2-(2-carboxyphenyl)-2H-indazol-5-yl]methyl-2-butyl-4-chloro-5 -(hydroxymethyl)-1-H-imidazole.

Workup

  1. customas obtained in Example 2
  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 twice with ion-exchanged water (1 ml)
  8. additionOne drop of conc. hydrochloric acid was added to the filtrate
  9. customto precipitate solid, which
  10. filtrationwas filtered off
  11. washwashed with water
  12. customThey were dried in vacuo at 37° C. for two days

Sources & evidence

ORD record
ord-c3afb03e28ad49d1a4d0fe4b56fa1760
Source dataset
uspto-grants-1995_02
Patent number
US05387684

Reaction notes

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