Ammonia → HCID 67119586, compound

HRID 2080156Notes

Reaction equation

HRID 2080156 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([CH:20](O)[C:21]3SC(C#N)=[CH:23][CH:22]=3)=[CH:19][C:14]=2[CH:13]=[CH:12]1.[NH3:29].[S:30]([O-])([O-])(=O)=O.[Mg+2].O1[CH2:40][CH2:39]CC1>>[CH:12]1[O:11][CH:15]=[CH:16][C:17]2[C:13]=1[CH:14]=[CH:19][C:18]=2[CH2:20][C:21]1[CH:22]=[CH:23][S:30][C:39]=1[CH2:40][NH2:29]

Participants

7

Reactant 6

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 24083Sulfuric acid magnesium salt (1:1)HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 23130740HCID 23130740, compound

Product 1

HCID 67119586HCID 67119586, compoundYield 82%

Procedure

To a solution of lithium aluminum hydride (488 mg, 12.9 mmol) in tetrahydrofuran (10 mL) was added aluminum chloride (1.72 g, 12.9 mmol) on an ice bath, and the solution was stirred for 10 minutes. 5-(Benzofuran-5-yl-hydroxy-methyl)-thiophene-2 carbonitrile described in Preparation Example 177 (364 mg, 1.43 mmol) was added to this suspension on an ice bath, and the solution was stirred for 3 hours. Aqueous ammonia was added to the reaction solution, then, anhydrous magnesium sulfate was added for drying, and the solution was filtered through Celite pad. The filtrate was concentrated in vacuo, the residue was purified by NH silica gel column chromatography (heptane/ethyl acetate=1/1), and the title compound (285 mg, 82%) was obtained as a light brown oil.

Workup

  1. additionwas added to this suspension on an ice bath
  2. stirringthe solution was stirred for 3 hours
  3. customfor drying
  4. filtrationthe solution was filtered through Celite pad
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by NH silica gel column chromatography (heptane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-3e63fbf5d5d84867b5f955f47706b94e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…