Water → HCID 178522844, compound

HRID 1297598Notes

Reaction equation

HRID 1297598 reaction equation
[C:1]([CH2:3][C:4]1[CH:27]=[CH:26][C:7]([CH2:8][NH:9][C:10](=[O:25])[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=2[O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:6]([F:28])[CH:5]=1)#[N:2].[N-:29]=[N+:30]=[N-:31].[Na+].Cl.C(N(CC)CC)C.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][C:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([NH:9][CH2:8][C:7]2[CH:26]=[CH:27][C:4]([CH2:3][C:1]3[NH:31][N:30]=[N:29][N:2]=3)=[CH:5][C:6]=2[F:28])=[O:25])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 17832839HCID 17832839, compound

Product 1

HCID 178522844HCID 178522844, compoundYield 296.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
116 °C

Procedure

N-(4-Cyanomethyl-2-fluoro-benzyl )-2-(4-fluoro-phenoxy)-nicotinamide (0.100 g) was combined with sodium azide (0.653 g) and triethylamine hydrochloride (0.334 g) in anhydrous toluene (4 mL). The reaction mixture was heated under nitrogen in a sealable tube in an oil bath (116° C.) overnight. The reaction mixture was then allowed to cool to ambient temperature. Water (10 mL) and ethyl acetate (10 mL) were added, and the organic layer was separated. The pH of the aqueous layer was adjusted to 3 with 3N hydrochloric acid. The aqueous layer was subsequently extracted with ethyl acetate (5×15 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography (acetic acid:methanol:dichloromethane=1:5:94) to yield the title compound (0.33 g).

Workup

  1. temperatureto cool to ambient temperature
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was subsequently extracted with ethyl acetate (5×15 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography (acetic acid:methanol:dichloromethane=1:5:94)

Sources & evidence

ORD record
ord-a1efd2889c3f4061864018f5b2fd15e4
Source dataset
uspto-grants-2007_07
Patent number
US07250518B2

Reaction notes

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