Trityl chloride → HCID 66768878, compound

HRID 606451Notes

Reaction equation

HRID 606451 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([S:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][N:11]=2)=[N:2]1.[C:18](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C1COCC1>[C:19]1([C:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:1]2[CH:5]=[N:4][C:3]([S:6][CH2:7][CH2:8][O:9][C:10]3[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][N:11]=3)=[N:2]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178510225HCID 178510225, compound

Product 1

HCID 66768878HCID 66768878, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{[2-(1H-1,2,4-triazol-3-ylthio)ethyl]oxy}pyridine-4-carbonitrile obtained in Reference Example 17 (3.40 g, 13.7 mmol), trityl chloride (5.73 g, 20.6 mmol) and triethylamine (2.87 mL, 20.6 mmol) in THF (30 mL) was stirred at room temperature for 15 hr. The mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate and water. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The obtained oil was purified by silica gel column chromatography (20%-40% ethyl acetate/hexane) to give the title compound as a white powder (5.37 g, 80%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate and water
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained oil was purified by silica gel column chromatography (20%-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3c64ea124b65499398bfa0b029ef2159
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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