Sodium sulfate decahydrate → HCID 59334641, compound

HRID 1639758Notes

Reaction equation

HRID 1639758 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:22]=[C:11]2[C:12]([CH:16]3[CH2:18][CH:17]3[CH:19]=[N:20]O)=[CH:13][CH:14]=[CH:15][N:10]2[N:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:7][C:8]1[N:22]=[C:11]2[C:12]([CH:16]3[CH2:18][CH:17]3[CH2:19][NH2:20])=[CH:13][CH:14]=[CH:15][N:10]2[N:9]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrate2×HCID 21226445Aluminium lithium hydride2×HCID 72257856HCID 72257856, compound

Product 1

HCID 59334641HCID 59334641, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of lithium aluminum hydride (150 mg, 3.24 mmol) in tetrahydrofuran (8 mL) was added a solution of 2-(2-methyl[1,2,4]triazolo[1,5-a]pyridin-8-yl)cyclopropanecarbaldehyde oxime (175 mg, 0.809 mmol) obtained in Reference Example 24 in tetrahydrofuran (8 mL) at room temperature, and the mixture was stirred at room temperature for 30 min. Sodium sulfate decahydrate (1.8 g) was added under ice-cooling, and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (8 mL), the solution was added to a suspension of lithium aluminum hydride (150 mg, 3.24 mmol) in tetrahydrofuran (8 mL) at 0° C., and the mixture was stirred at room temperature for 3 hr. Sodium sulfate decahydrate (1.8 g) was added under ice-cooling, and the mixture was filtered through celite to give the title compound (98.9 mg, yield 60%).

Workup

  1. temperaturecooling
  2. filtrationthe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in tetrahydrofuran (8 mL)
  5. stirringthe mixture was stirred at room temperature for 3 hr
  6. temperaturecooling
  7. filtrationthe mixture was filtered through celite

Sources & evidence

ORD record
ord-6f5cbd7121e24ab38a831ffdd753e12d
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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