1,2-Dichloroethane → 2-(2H-1,2,3-Triazol-2-yl)-N-(2-{[4-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)benzamide

HRID 1750591Notes

Reaction equation

HRID 1750591 reaction equation
C(N(CC)CC)C.N1C2C(=NC=CC=2)N(O)N=1.C(Cl)CCl.[F:22][C:23]([F:38])([F:37])[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([CH2:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH:32]2[NH2:36])[CH:25]=1.[N:39]1[N:40]([C:44]2[CH:52]=[CH:51][CH:50]=[CH:49][C:45]=2[C:46](O)=[O:47])[N:41]=[CH:42][CH:43]=1>C(Cl)Cl>[N:39]1[N:40]([C:44]2[CH:52]=[CH:51][CH:50]=[CH:49][C:45]=2[C:46]([NH:36][CH:32]2[CH2:33][CH2:34][CH2:35][CH:31]2[CH2:30][C:26]2[CH:25]=[C:24]([C:23]([F:22])([F:37])[F:38])[CH:29]=[CH:28][N:27]=2)=[O:47])[N:41]=[CH:42][CH:43]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acidHCID 1183082032-{[4-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine2×

Product 1

HCID 1183080702-(2H-1,2,3-Triazol-2-yl)-N-(2-{[4-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.099 ml, 0.71 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (0.039 g, 0.29 mmol) and EDC (0.055 g, 0.29 mmol) were added to a solution 2-{[4-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine (Intermediate 12; 0.058 g, 0.24 mmol) and 2-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1001401-62-2; 0.054 g, 0.29 mmol) in DCM (3 ml). The reaction was stirred at room temperature for 24 hours and then diluted with DCM (40 ml) and washed with a saturated solution of sodium bicarbonate (10 ml). The organics were dried over magnesium sulfate, filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-80% ethyl acetate/petrol) to afford the title compound.

Workup

  1. washwashed with a saturated solution of sodium bicarbonate (10 ml)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered through a hydrophobic frit
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica, 0-80% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-84124871f7f642d78a7077466e322ae9
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…