Cyanuric chloride → 4-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carbonitrile

HRID 2079833Notes

Reaction equation

HRID 2079833 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])=[N:5][N:4]=[C:3]1[C:17]12[CH2:24][CH2:23][C:20]([C:25]([NH2:27])=O)([CH2:21][CH2:22]1)[CH2:19][CH2:18]2.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:15])([F:14])[F:16])=[N:5][N:4]=[C:3]1[C:17]12[CH2:22][CH2:21][C:20]([C:25]#[N:27])([CH2:23][CH2:24]1)[CH2:19][CH2:18]2

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 207550404-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxamide

Product 1

HCID 671194154-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of carboxamide 1-E (0.64 g, 1.7 mmol) and cyanuric chloride (0.47 g, 2.53 mmol) in DMF (15 ml) was stirred at room temperature under a nitrogen atmosphere. After 2 h, DMF was removed in vacuo and the solid was redissolved in methylene chloride (100 ml). This solution was washed with saturated aqueous sodium bicarbonate and brine, dried (Na2SO4), and stripped to give 1-F as a pale yellow solid. MS (ESI+)=361.3 (M+1); 1H NMR (500 MHz, CDCl3): δ2.15 (6H, m), 2.22 (6H, m), 3.47 (3H, s), 7.51 (1H, m), 7.72 (2H, m), 7.87 (1H, m) ppm.

Workup

  1. customDMF was removed in vacuo
  2. dissolutionthe solid was redissolved in methylene chloride (100 ml)
  3. washThis solution was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-d486b7b5c3654a1080e6ba309932da2c
Source dataset
uspto-grants-2011_04
Patent number
US07932280B2

Reaction notes

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