Azide → HCID 178522791, compound

HRID 1297601Notes

Reaction equation

HRID 1297601 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([CH2:7][NH:8][C:9](=[O:24])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][C:11]=2[O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:5][CH:4]=1)#[N:2].[N-:27]=[N+:28]=[N-:29].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[F:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([NH:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]3[NH:29][N:28]=[N:27][N:2]=3)=[CH:26][CH:25]=2)=[O:24])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 33558AzideHCID 61221Dibutyltin oxideHCID 17832852HCID 17832852, compound

Product 1

HCID 178522791HCID 178522791, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

N-(4-Cyano-benzyl)-2-(4-fluoro-phenoxy)-nicotinamide (0.090 g) was placed in a sealable tube with anhydrous toluene (2 mL). Timethylsilyl azide (0.10 mL) was added, followed dibutyltin oxide (0.010 g) and the reaction mixture heated to 110° C. for 20 h. The reaction mixture was allowed to cool to ambient temperature, and quenched with 30% sodium bicarbonate (10 mL). Ethyl acetate (10 mL) was added and the aqueous layer collected. The organic layer was subsequently extracted with 30% sodium bicarbonate (2×10 mL). The combined aqueous portions were brought to pH 2 with 3N hydrochloric acid, and extracted with ethyl acetate (5×25 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated to dryness in vacuo to yield the title compound (0.040 g).

Workup

  1. temperatureto cool to ambient temperature
  2. customquenched with 30% sodium bicarbonate (10 mL)
  3. additionEthyl acetate (10 mL) was added
  4. customthe aqueous layer collected
  5. extractionThe organic layer was subsequently extracted with 30% sodium bicarbonate (2×10 mL)
  6. extractionextracted with ethyl acetate (5×25 mL)
  7. dry with materialThe combined organics were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-74f258a36f0f47dd8bcffaaca5b2cf20
Source dataset
uspto-grants-2007_07
Patent number
US07250518B2

Reaction notes

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