Potassium Hydroxide → 4-(4-Benzyl-5-morpholin-4-ylmethyl-4h-[1,2,4]triazol-3-yl)-3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-3'-carboxylic acid amide

HRID 6920Notes

Reaction equation

HRID 6920 reaction equation
[OH-:1].[K+].[CH2:3]([N:10]1[C:14]([CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[N:13][N:12]=[C:11]1[CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[C:33]([C:34]#[N:35])=[CH:32][CH:31]=[CH:30][N:29]=2)[CH2:24][CH2:23]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CC(O)(C)C>[CH2:3]([N:10]1[C:14]([CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[N:13][N:12]=[C:11]1[CH:22]1[CH2:23][CH2:24][N:25]([C:28]2[C:33]([C:34]([NH2:35])=[O:1])=[CH:32][CH:31]=[CH:30][N:29]=2)[CH2:26][CH2:27]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 103211954-(4-Benzyl-5-morpholin-4-ylmethyl-4h-[1,2,4]triazol-3-yl)-3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-3'-carbonitrile

Product 1

HCID 103442814-(4-Benzyl-5-morpholin-4-ylmethyl-4h-[1,2,4]triazol-3-yl)-3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-3'-carboxylic acid amideYield 85.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Powdered potassium hydroxide (95 mg, 1.68 mmol) was added to a solution of the carbonitrile of example 52 (250 mg, 0.56 mmol) in 2-Methyl-propan-2-ol (10 ml). The mixture was heated at 100° C. for 18 hr before evaporating under reduced pressure. The residue was purified by chromatography on silica gel using methanol and ammonium hydroxide in dichloromethane (5:0.5:95) as eluant to give the title compound (220 mg), as a white solid

Workup

  1. custombefore evaporating under reduced pressure
  2. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e304c46bb199409e93427fe99739240d
Source dataset
uspto-grants-2006_08
Patent number
US07084145B2

Reaction notes

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