Triethylamine → HCID 89580991, compound

HRID 1501124Notes

Reaction equation

HRID 1501124 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[CH3:46][O:47][C:48]1[C:53]([CH2:54][NH2:55])=[C:52]([C:56]([F:59])([F:58])[F:57])[CH:51]=[C:50]([CH3:60])[N:49]=1>ClCCl.O>[CH3:46][O:47][C:48]1[C:53]([CH2:54][NH:55][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)=[C:52]([C:56]([F:59])([F:57])[F:58])[CH:51]=[C:50]([CH3:60])[N:49]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 751824-Phenoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 83486524HCID 83486524, compound

Product 1

HCID 89580991HCID 89580991, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenoxybenzoic acid (640 mg, 3 mmol) in anhydrous dichloromethane (30 mL) were added 1H-benzo[d][1,2,3]triazol-1-ol (600 mg, 4.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (864 mg, 4.5 mmol) and triethylamine (1.1 g, 10 mmol). After stirring at room temperature for 0.5 hour, (2-methoxy-6-methyl-4-(trifluoromethyl)pyridin-3-yl)methanamine (0.47 g, 2.1 mmol) was added. After stirring at room temperature for 4 hours, to the mixture was added water (20 mL). The resultant mixture was extracted with dichloromethane (20 mL×2). Organic layers were combined and concentrated to give a residue. The residue was purified by chromatography (petroleum ether/ethyl acetate=1:1) to give N-((2-methoxy-6-methyl-4-(trifluoromethyl)pyridin-3-yl)methyl)-4-phenoxybenzamide (600 mg, 67.5%). LRMS (M+H) m/z: calcd 416.13. found 416. 1H NMR (300 MHz, CD3OD): δ 7.78 (d, J=8.7 Hz, 2H), 7.40 (t, J=7.8 Hz, 2H), 7.18 (t, J=7.2 Hz, 1H), 7.12 (s, 1H), 7.05 (d, J=8.1 Hz, 2H), 6.97 (d, J=8.7 Hz, 2H), 4.63 (s, 2H), 4.01 (s, 3H), 2.53 (s, 3H).

Workup

  1. stirringAfter stirring at room temperature for 4 hours, to the mixture
  2. extractionThe resultant mixture was extracted with dichloromethane (20 mL×2)
  3. concentrationconcentrated
  4. customto give a residue
  5. customThe residue was purified by chromatography (petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-19cb8f0d56414b26a45485eed97c3e3c
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…