Water → HCID 66769079, compound

HRID 606452Notes

Reaction equation

HRID 606452 reaction equation
[C:1]1([C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:8]2[CH:12]=[N:11][C:10]([S:13][CH2:14][CH2:15][O:16][C:17]3[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[CH:19][N:18]=3)=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[C:31]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:8]2[CH:12]=[N:11][C:10]([S:13][CH2:14][CH2:15][O:16][C:17]3[CH:22]=[C:21]([CH2:23][NH2:24])[CH:20]=[CH:19][N:18]=3)=[N:9]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66768878HCID 66768878, compound

Product 1

HCID 66769079HCID 66769079, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}ethyl)oxy]pyridine-4-carbonitrile obtained in Reference Example 19 (5.00 g, 10.2 mmol) in THF (40 mL) was added to a suspension of lithium aluminum hydride (0.775 g, 20.4 mmol) in THF (60 mL) at 0° C., and the mixture was stirred at room temperature for 7 hr. The mixture was cooled to 0° C., water and 1N aqueous sodium hydroxide solution were added, and the insoluble material was filtered off. The filtrate was dried over sodium sulfate, and concentrated. The obtained oil was purified by silica gel column chromatography (0-20% methanol/ethyl acetate) to give the title compound as a yellow oil (2.06 g, 41%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. filtrationthe insoluble material was filtered off
  3. dry with materialThe filtrate was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained oil was purified by silica gel column chromatography (0-20% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-e2af71962ed549dbb7c6cd6ae5ac0f6f
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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