Acetonitrile → 1-(2-isopropylphenyl)-3-(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)urea

HRID 62055

Reaction equation

HRID 62055 reaction equation
[F:1][C:2]([F:31])([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25]C(N=[N+]=[N-])=O)=[CH:21][CH:20]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].[CH:32]([C:35]1[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=1[NH2:37])([CH3:34])[CH3:33].[C:42](=[O:45])([O-])[O-].[Cs+].[Cs+].C(#[N:50])C>>[CH:32]([C:35]1[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=1[NH:37][C:42]([NH:50][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[N:17]=[CH:18][N:14]([C:11]3[CH:12]=[CH:13][C:8]([O:7][C:2]([F:1])([F:31])[C:3]([F:6])([F:5])[F:4])=[CH:9][CH:10]=3)[N:15]=2)=[CH:24][CH:23]=1)=[O:45])([CH3:34])[CH3:33]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 125612-IsopropylanilineHCID 904416672-(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetyl azide

Product 1

HCID 1186750381-(2-isopropylphenyl)-3-(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)ureaYield 22%

Conditions

Temperature
70 °C

Procedure

To a 20 mL vial, 2-(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetyl azide (0.100 g, 0.228 mmol) was suspended in acetonitrile (1.5 mL). The suspension was stirred in a pre-heated heating block at 70° C. for 2 hours. The suspension was cooled to room temperature, then 2-isopropylaniline (0.0339 g, 0.251 mmol) and cesium carbonate (0.0890 g, 0.274 mmol) were added. The reaction was allowed to stir for overnight at room temperature. The reaction was filtered through a fritted funnel. The filtrate was concentrated onto Celite® and purified by reverse phase chromatography using 5-100% acetonitrile/water as eluent to provide the title compound as a white solid (0.028 g, 22%).

Workup

  1. temperatureThe suspension was cooled to room temperature
  2. stirringto stir for overnight at room temperature
  3. filtrationThe reaction was filtered through a fritted funnel
  4. concentrationThe filtrate was concentrated onto Celite®
  5. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-e76fb66b66ca431fadcd51189f25119b
Source dataset
uspto-grants-2016_09
Patent number
US09445594B2

Linked notes

Loading…