Triethylamine → [(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethylamino}-pyridine-3-carbonyl)-amino]-acetic Acid Methyl Ester

HRID 11689

Reaction equation

HRID 11689 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6]([NH:12][CH2:13][C:14]([N:16]2[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:18][C@H:17]2[CH3:31])=[O:15])=[C:7]([CH:11]=1)[C:8](O)=[O:9].Cl.CN(C)CCCN=C=NCC.Cl.[CH3:45][O:46][C:47](=[O:50])[CH2:48][NH2:49].C(N(CC)CC)C>ClCCl>[CH3:45][O:46][C:47](=[O:50])[CH2:48][NH:49][C:8]([C:7]1[C:6]([NH:12][CH2:13][C:14]([N:16]2[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:18][C@H:17]2[CH3:31])=[O:15])=[N:5][CH:4]=[C:3]([Cl:2])[CH:11]=1)=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 696557655-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2r,5s)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethylamino}-nicotinic acid hydrochloride salt

Product 1

HCID 69655399[(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethylamino}-pyridine-3-carbonyl)-amino]-acetic Acid Methyl EsterYield 49.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethylamino}-nicotinic acid hydrochloride salt (0.060 g, 0.12 mmol) in dichloromethane (2 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.034 g, 0.18 mmol). The reaction was stirred at ambient temperature for 5 minutes. This was followed by addition of solution of glycine methyl ester hydrochloride (0.015 g, 0.12 mmol) and triethylamine (0.016 mL, 0.12 mmol) in dichloromethane (0.5 mL). The reaction was then stirred at ambient temperature overnight. The reaction was diluted with dichloromethane and washed with water. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.030 g).

Workup

  1. stirringThe reaction was then stirred at ambient temperature overnight
  2. washwashed with water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32b4e24e442647798c376efbe48e8069
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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