Triethylamine → HCID 178521836, compound

HRID 1666342

Reaction equation

HRID 1666342 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11](=[O:19])OC3C=CC=CC=3)=[CH:9][C:4]=2[N:3]=[N:2]1.Cl.[NH:21]1[CH2:26][CH2:25][C:24](=[CH:27][C:28]2[CH:29]=[C:30]([CH:42]=[CH:43][CH:44]=2)[O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][N:33]=2)[CH2:23][CH2:22]1.C(N(CC)CC)C.CCOC(C)=O>CS(C)=O>[NH:3]1[C:4]2[CH:9]=[C:8]([NH:10][C:11]([N:21]3[CH2:26][CH2:25][C:24](=[CH:27][C:28]4[CH:44]=[CH:43][CH:42]=[C:30]([O:31][C:32]5[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:34][N:33]=5)[CH:29]=4)[CH2:23][CH2:22]3)=[O:19])[CH:7]=[CH:6][C:5]=2[N:1]=[N:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 668761612-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochlorideHCID 178521835Phenyl 1H-benzo[d][1,2,3]triazol-5-ylcarbamate

Product 1

HCID 178521836HCID 178521836, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of phenyl 1H-benzo[d][1,2,3]triazol-5-ylcarbamate (0.15 g, 0.62 mmol, from Step 1) in DMSO (5 mL) was added 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (0.23 g, 0.62 mmol) (from Example 1, Step 5), followed by triethylamine (0.16 mL, 1.2 mmol). The reaction was stirred at 60° C. overnight. The reaction was cooled down and EtOAc (30 mL) was added. The organic layer was washed with water, saturated NH4Cl, and brine, dried over anhydrous Na2SO4, filtered and concentrated. Purification by column chromatography (0-5% MeOH/CH2Cl2) gave the desired compound as a foam (144 mg). MS (M+1): 495.1; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.76-8.80 (m, 1H) 8.54-8.56 (m, 1H) 8.20 (dd, 1H) 8.01-8.04 (m, 1H) 7.76-7.82 (m, 1H) 7.37-7.42 (m, 2H) 7.21 (d, 1H) 7.13 (d, 1H) 7.02-7.05 (m, 2H) 6.37-6.40 (m, 1H) 3.56 (t, 2H) 3.48 (t, 2H) 3.28-3.30 (m, 1H) 2.50-2.51 (m, 1H) 2.33-2.38 (m, 2H).

Workup

  1. temperatureThe reaction was cooled down
  2. washThe organic layer was washed with water, saturated NH4Cl, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fc2dcedb90a34263b2c1a31e5f7d4a3b
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Linked notes

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