Aluminium lithium hydride → HCID 59828837, compound

HRID 1191073Notes

Reaction equation

HRID 1191073 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:10][NH:11][C:12]2[S:13][C:14]([CH3:25])=[C:15]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[N:16]=2)[CH2:9][CH2:8]1>C1COCC1>[CH:7]1([CH2:10][NH:11][C:12]2[S:13][C:14]([CH3:25])=[C:15]([C:17]3[CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[CH:23][CH:24]=3)[N:16]=2)[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59828831HCID 59828831, compound

Product 1

HCID 59828837HCID 59828837, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add a solution of 1M lithium aluminum hydride in THF (4.6 mL, 4.6 mmol) over 5 min to a solution of 4-(2-cyclopropylmethylamino-5-methyl-thiazol-4-yl)-benzonitrile (410 mg, 1.52 mmol) in anhydrous THF (10 mL). Heat to reflux for 30 min, cool to room temperature and quench by dropwise addition of water (5 mL), ether (50 mL), 3N NaOH (5 mL) and additional water (15 mL). Stir vigorously for 30 min and filter over a bed of Celite®. Wash the filtrate with water (2×100 mL) and brine (100 mL). Dry the organic phase over MgSO4, filter and concentrate in vacuo to obtain the title compound as a yellow oil (340 mg, 82%) that was used without further purification. MS (ES+) m/z: 274 (M+H)+.

Workup

  1. temperatureHeat
  2. temperatureto reflux for 30 min
  3. customquench by dropwise addition of water (5 mL), ether (50 mL), 3N NaOH (5 mL) and additional water (15 mL)
  4. filtrationfilter over a bed of Celite®
  5. washWash the filtrate with water (2×100 mL) and brine (100 mL)
  6. dry with materialDry the organic phase over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-7b98979526734fcfbd5f6db7788cf412
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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