2-Aminobiphenyl → 1-([1,1'-biphenyl]-2-yl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)urea

HRID 62046

Reaction equation

HRID 62046 reaction equation
[C:1](Cl)(=[O:5])C(Cl)=O.[F:7][C:8]([F:29])([F:28])[O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[N:19][C:18]([C:21]3[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=3)=[N:17]2)=[CH:12][CH:11]=1.C(N(CC)CC)C.[C:37]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]([NH2:43])=[CH:39][CH:40]=[CH:41][CH:42]=1>O1CCCC1>[C:37]1([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH:43][C:1]([NH:25][C:24]1[CH:26]=[CH:27][C:21]([C:18]2[N:19]=[CH:20][N:16]([C:13]3[CH:12]=[CH:11][C:10]([O:9][C:8]([F:7])([F:28])[F:29])=[CH:15][CH:14]=3)[N:17]=2)=[CH:22][CH:23]=1)=[O:5]

Participants

6

Reactant 4

HCID 70152-AminobiphenylHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 578244904-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)aniline

Product 1

HCID 1186751681-([1,1'-biphenyl]-2-yl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a three-necked round bottomed flask equipped with condenser and nitrogen inlet was charged with oxalyl chloride (0.378 g, 2.98 mmol). Tetrahydrofuran (25 mL) was added and the reaction was cooled to 0° C. 4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)aniline (0.800 g, 2.50 mmol) and triethylamine (1.74 mL, 12.5 mmol) were added at 0° C. After 30 minutes, [1,1′-biphenyl]-2-amine (0.508 g, 3.00 mmol) dissolved in tetrahydrofuran (25 mL) was added to the reaction mixture. The resulting reaction mixture was slowly warmed to room temperature. Upon completion, the reaction mixture was quenched with water (50 mL) and extracted with ethyl acetate (150 mL×2). The organic phase was washed with brine (50 mL). The combined organic layers were dried over sodium sulfate and were then concentrated under reduced pressure. Purification by flash column chromatography using 0-30% ethyl acetate/hexanes provided the title compound as an off white solid (0.560 g, 87%).

Workup

  1. customTo a three-necked round bottomed flask equipped with condenser and nitrogen inlet
  2. additionwas added to the reaction mixture
  3. customThe resulting reaction mixture
  4. temperaturewas slowly warmed to room temperature
  5. customUpon completion, the reaction mixture was quenched with water (50 mL)
  6. extractionextracted with ethyl acetate (150 mL×2)
  7. washThe organic phase was washed with brine (50 mL)
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. concentrationwere then concentrated under reduced pressure
  10. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-aaac296116d74832a9190249f138b063
Source dataset
uspto-grants-2016_09
Patent number
US09445594B2

Linked notes

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