1-Hydroxybenzotriazole → HCID 11500276, compound

HRID 422265Notes

Reaction equation

HRID 422265 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH2:9])=[N:7][OH:8])=[CH:4][CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[C:19][CH2:20][CH2:21][C:22](O)=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>O1CCOCC1>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:9]=[C:22]([CH2:21][CH2:20][C:19]#[C:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=3)[O:8][N:7]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 5930004-Fluoro-n-hydroxybenzimidamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66598382HCID 66598382, compound

Product 1

HCID 11500276HCID 11500276, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of commercially available 4-fluoro-N′-hydroxybenzamidine (220 mg, 1.4 mmol), 5-(pyridin-2-yl)pent-4-ynoic acid (330 mg, 1.4 mmol), HOBT (210 mg, 1.4 mmol) and EDCI.HCl (400 mg, 2.1 mmol) in dioxane (4.5 mL) was stirred at R.T for 7H, The reaction mixture was then heated at 100° C. for 36 h. The solvent was removed under reduced pressure and the residue was dissolved in DCM. The organic layer was washed with water, 1N NaOH and water. The organic layer was dried over Na2SO4, filtered and evaporated. Purification by flash chromatography (prepacked 10 g silicagel column, DCM/MeOH 99/1 as eluent) to afford 103 mg of 2-(4-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)but-1-ynyl)pyridine (Yield: 25%) as a yellow oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in DCM
  3. washThe organic layer was washed with water, 1N NaOH and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash chromatography (prepacked 10 g silicagel column, DCM/MeOH 99/1 as eluent)

Sources & evidence

ORD record
ord-a95b6a832e7d47a3a505f5e925ba5fb6
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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