HCID 18461111, compound → HCID 18461117, compound

HRID 2303343Notes

Reaction equation

HRID 2303343 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25]CC(=O)N(C)C)[CH2:21][CH2:20]3)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:21][N:22]([CH3:25])[CH3:23])[CH2:21][CH2:20]3)=[CH:11][C:12]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 18461111HCID 18461111, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18461117HCID 18461117, compoundYield 185.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of the amide from Step A (82 mg, 0.195 mmol) in 3 mL tetrahydrofuran was added lithium aluminum hydride (1.0M in tetrahydrofuran, 0.39 mL, 0.39 mmol) dropwise. After refluxing for 3 hours, the reaction was quenched with few drops of saturated Na2SO4, and then solvent was removed in vacuo. Purification by silica gel chromatography afforded the title compound (71 mg, 89%). NMR 1.8(m, 2H), 2.4(s, 6H0, 2.4(m, 4H).

Workup

  1. temperatureAfter refluxing for 3 hours
  2. customthe reaction was quenched with few drops of saturated Na2SO4
  3. customsolvent was removed in vacuo
  4. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-59a4404330e24a8a8d0b0fddadeacc45
Source dataset
uspto-grants-2002_08
Patent number
US06432980B1

Reaction notes

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