Aluminium lithium hydride → HCID 178434646, compound

HRID 57296Notes

Reaction equation

HRID 57296 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([C:14]3[C:15]([CH3:20])=[N:16][NH:17][C:18]=3[NH2:19])=[N:11][C:10]=2[CH:21]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH2:19][C:18]1[NH:17][N:16]=[C:15]([CH3:20])[C:14]=1[C:12]1[S:13][C:9]2[CH:8]=[CH:7][C:6]([CH2:4][OH:3])=[CH:21][C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 131728565Sodium sulfate nonahydrateHCID 178468708HCID 178468708, compound

Product 1

HCID 178434646HCID 178434646, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-5-carboxylic acid ethyl ester (30 mg) in THF (1 mL) was added lithium aluminum hydride (4 mg). The reaction mixture was stirred at room temperature for 5 hrs at which point sodium sulfate nonahydrate was added. The resulting mixture was stirred for an additional 30 min. The solids were removed by filtration. The solvent was then evaporated and the residue was purified by flash column chromatography eluting with CHCl3:MeOH=9:1 to yield 21 mg (81%) of the title compound as a cream coloured solid. MS (m/z, ES+): 261.1 (M+1,100%).

Workup

  1. additionwas added
  2. customThe solids were removed by filtration
  3. customThe solvent was then evaporated
  4. customthe residue was purified by flash column chromatography
  5. washeluting with CHCl3

Sources & evidence

ORD record
ord-a8c2d0d7d31f4537a521925f7eb9e4f6
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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