Tetrabutylammonium Fluoride → HCID 121268893, compound

HRID 2199631Notes

Reaction equation

HRID 2199631 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[N:16]=[N:15][C:14]([C:17]2[CH:18]=[C:19]([C:23]#[C:24][C:25]3[CH:26]=[C:27]([NH:31][C:32]([C:34]4[O:35][CH:36]=[CH:37][C:38]=4[CH3:39])=[O:33])[CH:28]=[CH:29][CH:30]=3)[CH:20]=[N:21][CH:22]=2)=[N:13]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[N:16]=[N:15][C:14]([C:17]2[CH:18]=[C:19]([C:23]#[C:24][C:25]3[CH:26]=[C:27]([NH:31][C:32]([C:34]4[O:35][CH:36]=[CH:37][C:38]=4[CH3:39])=[O:33])[CH:28]=[CH:29][CH:30]=3)[CH:20]=[N:21][CH:22]=2)=[N:13]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735699HCID 131735699, compound

Product 1

HCID 121268893HCID 121268893, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of N-(3-((5-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)pyridin-3-yl)ethynyl)phenyl)-3-methylfuran-2-carboxamide (71 mg, 0.131 mmol, 1 eq) in anhydrous THF (2.6 mL) under nitrogen atmosphere at 0° C. was added dropwise a solution of tetrabutylammonium fluoride (1.0 M in THF, 0.393 mL, 3 eq). The clear reaction solution was stirred at 0° C. using an ice-bath for 3 hours. The solution was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was isolated, washed with aqueous ammonium chloride, brine, and dried with anhydrous sodium sulfate. The upper clear liquor was decanted, concentrated, and the oily residue was loaded onto silica and chromatographed (EtOAc-Hex 1:4 to 4:1) to yield N-[3-({5-[2-(3-hydroxypropyl)-2H-tetrazol-5-yl]pyridin-3-yl}ethynyl)phenyl]-3-methyl-2-furamide as a white solid in the amount of 28 mg.

Workup

  1. customfor 3 hours
  2. customThe solution was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. customThe organic layer was isolated
  4. washwashed with aqueous ammonium chloride, brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe upper clear liquor was decanted
  7. concentrationconcentrated
  8. customchromatographed (EtOAc-Hex 1:4 to 4:1)

Sources & evidence

ORD record
ord-71bd8a197fd54090ac26aca3e8a8e58f
Source dataset
uspto-grants-2016_06
Patent number
US09359336B2

Reaction notes

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