N,N-Dimethylglycine → N-(5-Chloro-2-(2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy)-benzyl)-2-diethylamino-acetamide

HRID 480196Notes

Reaction equation

HRID 480196 reaction equation
CN(C)CC(O)=[O:5].[NH2:8][CH2:9][C:10]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:11]=1[O:12][CH2:13][C:14]([N:16]1[CH2:21][C@H:20]([CH3:22])[N:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:18][C@H:17]1[CH3:31])=[O:15].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH2:58]([N:60]([CH2:63][CH3:64])[CH2:61][CH3:62])[CH3:59]>ClCCl.C(=O)(O)[O-].[Na+]>[Cl:36][C:34]1[CH:33]=[CH:32][C:11]([O:12][CH2:13][C:14]([N:16]2[CH2:21][CH: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][CH:17]2[CH3:31])=[O:15])=[C:10]([CH:35]=1)[CH2:9][NH:8][C:59](=[O:5])[CH2:58][N:60]([CH2:63][CH3:64])[CH2:61][CH3:62]

Participants

8

Reactant 5

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 54187452HCID 54187452, compound

Product 1

HCID 18768106N-(5-Chloro-2-(2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy)-benzyl)-2-diethylamino-acetamideYield 90.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N,N-dimethylglycine (0.014 g, 0.13 mmol) and (2R,5S)-2-(2-aminomethyl-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.063 g, 0.15 mmol) in dichloromethane (2 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.034 g, 0.18 mmol), 1-hydroxybenzotriazole (0.021 g, 0.15 mmol), and triethylamine (0.036 mL, 0.36 mmol). After the reaction was stirred for 48 hours, the solution was diluted with saturated aqueous sodium bicarbonate and extracted with dichloromethane (3×). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.063 g, 80%).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45887329159849a69a136c4ac02eb92c
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

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