Sodium Hydroxide → HCID 23117106, compound

HRID 1921260Notes

Reaction equation

HRID 1921260 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[N:14][NH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C1(C)C=CC=CC=1.O1CCOCC1>CCO>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)=[N:14][N:15]2[CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 748271-(2-Chloroethyl)piperidineHCID 21840791Dioxane tolueneHCID 178420376HCID 178420376, compound

Product 1

HCID 23117106HCID 23117106, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-benzyloxy-3-cyclopentyl-1H-indazole was heated for 1 hour with NaOH (1.64 g, 41 mmol) and 1-(2-chloroethyl)piperidine in EtOH (60 ml) at 40° C. The reaction was followed by TLC (toluene/dioxane: 7/3), and when completed, the mixture was cooled to room temperature. The mixture was quenched by NH4Cl, extracted with AcOEt, dried over Na2SO4, filtered and concentrated under vacuum. Purification by flash chromatography (toluene/1,4-dioxane 7/3) gave the expected product (600 mg, 8% as solid).

Workup

  1. customThe mixture was quenched by NH4Cl
  2. extractionextracted with AcOEt
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification by flash chromatography (toluene/1,4-dioxane 7/3)

Sources & evidence

ORD record
ord-a2fc36b07580485f92e12bcf34178514
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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