Triethylamine → HCID 69911897, compound

HRID 480198Notes

Reaction equation

HRID 480198 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].[O:30]=[C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33](=[O:40])[N:32]1[CH2:41][CH2:42][S:43](Cl)(=[O:45])=[O:44].C(N(CC)CC)C>C(Cl)Cl.C(=O)([O-])O.[Na+]>[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:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:6]([CH:9]=1)[CH2:7][NH:8][S:43]([CH2:42][CH2:41][N:32]1[C:31](=[O:30])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]1=[O:40])(=[O:44])=[O:45]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3087392-Phthalimidoethanesulfonyl chlorideHCID 54187452(2R,5S)-2-(2-Aminomethyl-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone

Product 1

HCID 69911897HCID 69911897, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl amine (0.060 g, 0.143 mmol) in methylene chloride (3 mL) was added 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonyl chloride (0.043 g, 0.150 mmol) and triethylamine (0.060 mL, 0.43 mmol) and the solution was stirred 1 hr at ambient temperature. The reaction was diluted with saturated aqueous sodium hydrogen carbonate and extracted with methylene chloride. The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.073 g, 77%).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cffd577bb1da4587becae13283655a30
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Reaction notes

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