Lithium aluminum hydride → HCID 53250984, compound

HRID 1627739Notes

Reaction equation

HRID 1627739 reaction equation
[AlH4-].[Li+].C([O:5][C:6](=O)[CH2:7][N:8]1[C:12]([CH2:13][CH2:14][C:15]2[N:26]=[C:18]3[C:19]([O:24][CH3:25])=[CH:20][CH:21]=[C:22]([CH3:23])[N:17]3[N:16]=2)=[N:11][C:10]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:9]1)C>O1CCCC1>[CH3:25][O:24][C:19]1[C:18]2[N:17]([N:16]=[C:15]([CH2:14][CH2:13][C:12]3[N:8]([CH2:7][CH2:6][OH:5])[N:9]=[C:10]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:11]=3)[N:26]=2)[C:22]([CH3:23])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 53250983HCID 53250983, compound

Product 1

HCID 53250984HCID 53250984, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1M of Lithium tetrahydroaluminate in Tetrahydrofuran (5.0 mL) was added to a stirred solution of {5-[2-(8-Methoxy-5-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-ethyl]-3-phenyl-1,2,4-triazol-1-yl}-acetic acid ethyl ester (950 mg, 2.2 mmol) in Tetrahydrofuran (3 mL) at rt. The reaction is exothermic. The solution was stirred at rt under Ar 3 h. The solution was diluted with THF (10 ml) and quenched by adding wet Na2SO4. The solution was filtered through dry Na2SO4, and was rotovaped. The crude product was purified by silica gel chromatography (Eluent: 0-30% MeOH in EtOAc). Yield: 710 mg (75%) of the title compound as a clear oil. LC-MS: m/z=379.4 (MH+), tR=0.51 min, Method B.

Workup

  1. customquenched
  2. additionby adding wet Na2SO4
  3. filtrationThe solution was filtered through dry Na2SO4
  4. customThe crude product was purified by silica gel chromatography (Eluent: 0-30% MeOH in EtOAc)

Sources & evidence

ORD record
ord-d9dfe31d83624287a47c0e37552b5c72
Source dataset
uspto-grants-2014_07
Patent number
US08785653B2

Reaction notes

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