Aluminium lithium hydride → HCID 72572534, compound

HRID 1191067Notes

Reaction equation

HRID 1191067 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:10][NH:11][C:12]2[S:16][N:15]=[C:14]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[CH:13]=2)[CH2:9][CH2:8]1>C1COCC1>[NH2:15][C:14]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[CH:23][CH:24]=1)=[CH:13][C:12](=[S:16])[NH:11][CH2:10][CH:7]1[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59828916HCID 59828916, compound

Product 1

HCID 72572534HCID 72572534, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add 1M lithium aluminum hydride in THF (3.0 mL, 3.0 mmol) to a solution of 4-[5-(cyclopropylmethyl-amino)-isothiazol-3-yl]-benzonitrile (210 mg, 0.82 mmol) in THF (8 mL) at room temperature under a nitrogen atmosphere. Stir the mixture at ambient temperature for 45 min, then quench the reaction sequentially with water (0.3 mL) and 5N aqueous NaOH (0.3 mL). Filter the slurry through Celite®, dry the filtrate over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel (8 g) eluting with DCM/2M ammonia in methanol (20:1) to obtain the desired intermediate (110 mg, 51%). MS (ES+) m/z: 245.1 (M-NH3+H)+.

Workup

  1. customquench
  2. customthe reaction sequentially with water (0.3 mL) and 5N aqueous NaOH (0.3 mL)
  3. filtrationFilter the slurry through Celite®
  4. dry with materialdry the filtrate over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by chromatography on silica gel (8 g)
  8. washeluting with DCM/2M ammonia in methanol (20:1)

Sources & evidence

ORD record
ord-f6a6c5a103c14e13829cbea8b396a8b8
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…