HCID 18007553, compound → HCID 54134444, compound

HRID 988107Notes

Reaction equation

HRID 988107 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:9]([CH2:12][CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH:23]3[CH2:28][CH2:27][N:26]([C:29](OC(C)(C)C)=O)[CH2:25][CH2:24]3)[CH:21]=2)[CH:16]=[N:15]1)[CH2:10][CH3:11])[CH3:8]>C1COCC1>[CH2:7]([N:9]([CH2:12][CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)[CH:21]=2)[CH:16]=[N:15]1)[CH2:10][CH3:11])[CH3:8]

Participants

4

Reactant 2

HCID 18007553HCID 18007553, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54134444HCID 54134444, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of LAH in THF (1M, 0.25 mL, 0.25 mmol) was added to a solution of 1-(2-(N,N-diethylamino)ethyl)-6-(N-Boc-tetrahydro-4-pyridinyl)-1H-indazole (10.2 mg, 0.025 mmol) in THF (0.5 mL) at room temperature under argon and the resulting solution was refluxed for 2 h. After cooling to room temperature, the reaction was quenched using sodium sulfate decahydrate solid and the resulting solid was removed by filtration, extracting the product into ethyl acetate. The solvent was removed in vacuo and purification using an SPE (solid phase extraction) cartridge containing 1 g of silica gel by eluting with 0-10% 2M methanolic ammonia in dichloromethane yielded 1-(2-(N,N-diethylamino)ethyl)-6-(N-methyltetrahydro4-pyridinyl)-1H-indazole (5.9 mg, 74%).

Workup

  1. temperaturethe resulting solution was refluxed for 2 h
  2. customthe reaction was quenched
  3. customthe resulting solid was removed by filtration
  4. extractionextracting the product into ethyl acetate
  5. customThe solvent was removed in vacuo and purification
  6. extractionan SPE (solid phase extraction) cartridge
  7. additioncontaining 1 g of silica gel
  8. washby eluting with 0-10% 2M methanolic ammonia in dichloromethane

Sources & evidence

ORD record
ord-7ac0fb59e9654580aaf6190715642cec
Source dataset
uspto-grants-2003_10
Patent number
US06635639B2

Reaction notes

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