Ammonium Hydroxide → 4-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxamide

HRID 2079832Notes

Reaction equation

HRID 2079832 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]([OH:27])=O)([CH2:21][CH2:22]1)[CH2:19][CH2:18]2.C(N1C=CN=C1)([N:30]1C=CN=C1)=O.[OH-].[NH4+]>C(Cl)Cl.O>[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:14])[F:15])=[N:5][N:4]=[C:3]1[C:17]12[CH2:22][CH2:21][C:20]([C:25]([NH2:30])=[O:27])([CH2:19][CH2:18]1)[CH2:23][CH2:24]2

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 592555694-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A portion of carboxylic acid 1-D (0.67 g, 1.77 mmol) was suspended in methylene chloride (15 ml) and treated with 1,1′-carbonyldiimidazole (0.57 g, 3.52 mmol) at room temperature and under a nitrogen atmosphere. After 2 h, concentrated ammonium hydroxide was added (40 ml) and the reaction was stirred for 18 h. The crude mixture was diluted with water (150 ml) and extracted with 3 portions of methylene chloride (70 ml). The organic washes were combined, washed with brine, dried (Na2SO4), and stripped to yield 1-E as a white powder. MS (ESI+)=379.3 (M+1); 1H NMR (500 MHz, CDCl3): δ 7.88-7.86 (m, 1 H), 7.75-7.71 (m, 2 H), 7.54 (t, 1 H), 5.75 (s, 1 H), 5.47 (s, 1 H), 3.50 (s, 3 H), 2.22 (t, 6 H), 2.00 (t, 6 H) ppm.

Workup

  1. extractionextracted with 3 portions of methylene chloride (70 ml)
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-3ac2dc7cecb043c0a4bdc62c736bdb7a
Source dataset
uspto-grants-2011_04
Patent number
US07932280B2

Reaction notes

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