Water → HCID 57656248, compound

HRID 2041445Notes

Reaction equation

HRID 2041445 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:11]1[S:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:14]=2[N:15]=1)[CH:8]([CH3:10])[CH3:9].O.[OH-].[Na+]>C1COCC1>[NH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:13]2[S:12][C:11]([CH2:7][CH:8]([CH3:9])[CH3:10])=[N:15][C:14]=2[CH:16]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66707196HCID 66707196, compound

Product 1

HCID 57656248HCID 57656248, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add lithium aluminum hydride (0.78 mL, 0.78 mmol, 1M solution in THF) to 2-isobuty-benzothiazole-5-carbonitrile (113 mg, 0.52 mmol) in THF (5 mL) and stir for 4 h at room temperature. Add water (0.27 mL), 2N sodium hydroxide (0.27 mL) and water (0.37 mL). Filter the precipitate and wash the filtrate with brine. Dry over Na2SO4 and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:1) and then 1M ammonia in methanol/dichloromethane (1:9). Purify the polar fraction by SCX chromatography to give the title compound (63 mg, 55%). MS (ES+) m/z: 221 (M+H+).

Workup

  1. filtrationFilter the precipitate
  2. washwash the filtrate with brine
  3. dry with materialDry over Na2SO4
  4. concentrationconcentrate in vacuo
  5. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:1)
  6. customPurify the polar fraction by SCX chromatography

Sources & evidence

ORD record
ord-85a08fcd99d5471eb80388605733d8aa
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

Loading…