HCID 20270304, compound → HCID 20199146, compound

HRID 485388Notes

Reaction equation

HRID 485388 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8](=O)[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:14]=2)=[N:5][C:4]([C:27](OC)=[O:28])=[N:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:14]=2)=[N:5][C:4]([CH2:27][OH:28])=[N:3]1

Participants

4

Reactant 2

HCID 20270304HCID 20270304, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20199146HCID 20199146, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of methyl 1-methyl-5-[[1-oxo-4-[3-(1-piperidinylmethyl)phenoxy]butyl]amino]-1H-1,2,4-triazole-3-carboxylate (1.25 g) and lithium aluminium hydride (1.0 g) in tetrahydrofuran (30 ml) was stirred under nitrogen at room temperature for 5 h, cooled to 0° and quenched with water. The mixture was diluted with ethyl acetate, filtered and the filtrate was evaporated in vacuo. The residue was chromatographed to give an oil, which crystallised on trituration with ether to yield the title compound as a white solid (0.33 g) m.p. 84°-5°, tlc System B,Rf 0.6.

Workup

  1. temperaturecooled to 0°
  2. customquenched with water
  3. additionThe mixture was diluted with ethyl acetate
  4. filtrationfiltered
  5. customthe filtrate was evaporated in vacuo
  6. customThe residue was chromatographed
  7. customto give an oil, which
  8. customcrystallised on trituration with ether

Sources & evidence

ORD record
ord-5b581e076bbf4538bf43e37b380145a0
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

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