1H-Indazole → HCID 68074357, compound

HRID 530863Notes

Reaction equation

HRID 530863 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4]1.[C:12]([O:16][C:17](=[O:27])[NH:18][CH:19]1[CH2:26][CH2:25][CH2:24][C:21]2([O:23][CH2:22]2)[CH2:20]1)([CH3:15])([CH3:14])[CH3:13]>CN(C=O)C>[N:3]1([CH2:22][C:21]2([OH:23])[CH2:24][CH2:25][CH2:26][C@@H:19]([NH:18][C:17](=[O:27])[O:16][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:20]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4]1

Participants

5

Reactant 3

HCID 92211H-IndazoleHCID 24758Sodium hydrideHCID 130067861HCID 130067861, compound

Product 1

HCID 68074357HCID 68074357, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (1.1 mmol) was added to a vial containing indazole (2.2 mmol) in DMF (1 ml). The mixture was stirred at rt for 15 mins, then added tert-butyl-1-oxaspiro[2.5]octaN-5-ylcarbamate (0.22 mmol). The reaction was stirred at 60° C. overnight. Upon completion, the mixture was quenched by water (3 mL). The mixture was extracted using dichloromethane (3×5 mL). The extracts were combined and dried using anhydrous sodium sulfate. The product was purified using HPLC.

Workup

  1. stirringThe reaction was stirred at 60° C. overnight
  2. customUpon completion, the mixture was quenched by water (3 mL)
  3. extractionThe mixture was extracted
  4. customdried
  5. customThe product was purified

Sources & evidence

ORD record
ord-5e4310e12b7f4a7b8f0adb2ed95afd81
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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