Methanol → HCID 69912619, compound

HRID 480197Notes

Reaction equation

HRID 480197 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:6]([CH:9]=1)[CH2:7][NH2:8].N1C=CC=CC=1.[C:36]([NH:39][CH2:40][CH2:41][NH2:42])(=[O:38])[CH3:37].[CH3:43][OH:44]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([N:14]2[CH2:19][CH:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH2:16][CH:15]2[CH3:29])=[O:13])=[C:6]([CH:9]=1)[CH2:7][NH:8][C:43](=[O:44])[NH:42][CH2:41][CH2:40][NH:39][C:36](=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 66082N-(2-aminoethyl)acetamideHCID 54187452(2R,5S)-2-(2-Aminomethyl-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone

Product 1

HCID 69912619HCID 69912619, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylamine (0.200 g, 0.477 mmol) in methylene chloride (10 mL) was added pyridine (0.077 mL, 0.954 mmol) and 4-nitro phenyl chloroformate (0.097 g, 0.525 mmol). The resulting mixture was stirred for one hour at ambient temperature and then concentrated in vacuo. The residue (0.055 g, 0.094 mmol) was dissolved in methanol (1 mL). N-Acetylethylenediamine (0.019 mL, 0.188 mmol) was added and the reaction was stirred at room temperature over night. The reaction was concentrated in vacuo and chromatography on silica gel gave the title compound (0.019 g, 27%).

Workup

  1. concentrationconcentrated in vacuo
  2. stirringthe reaction was stirred at room temperature over night
  3. concentrationThe reaction was concentrated in vacuo and chromatography on silica gel

Sources & evidence

ORD record
ord-56b3f9561b23468a899e981436e54c3a
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

Loading…