Tetrahydrofuran → HCID 17974512, compound

HRID 2252324Notes

Reaction equation

HRID 2252324 reaction equation
[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([S:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:20]O)[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2].C1C=CC(P([N:36]=[N+:37]=[N-:38])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1.C1COCC1>C1(C)C=CC=CC=1>[N:36]([CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[S:13][C:10]1[CH:11]=[CH:12][C:7]2[N:8]([C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][N:6]=2)[CH:9]=1)=[N+:37]=[N-:38]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 10357392HCID 10357392, compound

Product 1

HCID 17974512HCID 17974512, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of [2-(3-Isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-ylsulfanyl)-phenyl]-methanol (254.0 mg, 0.85 mmol) and DPPA (220 μL, 1.02 mmol) in toluene (8.5 mL, 0.10 M) at 0° C. was added DBU (152.0 μL, 1.02 mmol), followed by the addition of THF (1 mL). The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The reaction mixture was quenched with NaHCO3, and extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (eluting with 2% methanol/ethyl acetate) to give the title compound as an oil (228 mg, 83%). MS (M+1)=370.5.

Workup

  1. customThe reaction mixture was quenched with NaHCO3
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (eluting with 2% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-04b3a7e0b30744659572aecc82dc12dc
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

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