Triethylamine → 2-{3,5-Dichloro-4-[3-(cis-3,5-dimethyl-piperidine-1-carbonyl)-4-hydroxy-phenoxy]-phenyl}-2H-[1,2,4]triazine-3,5-dione

HRID 1006224Notes

Reaction equation

HRID 1006224 reaction equation
O=C1CCC(=O)N1[O:8][C:9](=O)[C:10]1[CH:15]=[C:14]([O:16][C:17]2[C:22]([Cl:23])=[CH:21][C:20]([N:24]3[C:29](=[O:30])[NH:28][C:27](=[O:31])[CH:26]=[N:25]3)=[CH:19][C:18]=2[Cl:32])[CH:13]=[CH:12][C:11]=1[OH:33].C(N(CC)CC)C.[CH3:42][C@H:43]1[CH2:48][C@@H:47]([CH3:49])[CH2:46][NH:45][CH2:44]1>C(COC)OC>[Cl:32][C:18]1[CH:19]=[C:20]([N:24]2[C:29](=[O:30])[NH:28][C:27](=[O:31])[CH:26]=[N:25]2)[CH:21]=[C:22]([Cl:23])[C:17]=1[O:16][C:14]1[CH:13]=[CH:12][C:11]([OH:33])=[C:10]([C:9]([N:45]2[CH2:46][C@H:47]([CH3:49])[CH2:48][C@H:43]([CH3:42])[CH2:44]2)=[O:8])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 641101rel-(3R,5S)-3,5-DimethylpiperidineHCID 865938795-[2,6-dichloro-4-(3,5-dioxo-4,5-dihydro-3H-(1,2,4]triazin-2-yl)-phenoxy]-2-hydroxy-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Product 1

HCID 697081752-{3,5-Dichloro-4-[3-(cis-3,5-dimethyl-piperidine-1-carbonyl)-4-hydroxy-phenoxy]-phenyl}-2H-[1,2,4]triazine-3,5-dione

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To solution of 5-[2,6-dichloro-4-(3,5-dioxo-4,5-dihydro-3H-(1,2,4]triazin-2-yl)-phenoxy]-2-hydroxy-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester (320 mg) and triethylamine (265 μL) in dimethoxyethane (1.3 mL) was added 3,5-cis-dimethylpiperidine (189 mg). After 2 h, the reaction solution was concentrated in vacuo and flash chromatographed on silica gel (50% ethyl acetate/hexanes) to afford the title compound of this Example as a colorless solid, 130 mg. MS Calc.:505.3 Found:505.2

Workup

  1. concentrationthe reaction solution was concentrated in vacuo and flash
  2. customchromatographed on silica gel (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-beff4f1970c04db3b6b4ea3d0b798df9
Source dataset
uspto-grants-2004_09
Patent number
US06787652B1

Reaction notes

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