1,2-Dichloroethane → 2-[3-oxo-1-(toluene-4-sulfonyl)-piperazin-2-yl]-N-[6-(1-piperidin-1-ylmethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1(R)-yl]-acetamide

HRID 747051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747051
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:3]1[CH2:18][C:19]([OH:21])=O.[N:22]1([CH2:28][C:29]([C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[C@H:37]([NH2:41])[CH2:36][CH2:35][CH2:34]3)=[CH2:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:3]1[CH2:18][C:19]([NH:41][C@H:37]1[C:38]2[C:33](=[CH:32][C:31]([C:29]([CH2:28][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH2:30])=[CH:40][CH:39]=2)[CH2:34][CH2:35][CH2:36]1)=[O:21]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 591678696-(1-piperidin-1-ylmethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1(R)-ylamineHCID 620340531-[(4-methylphenyl)sulfonyl]-3-oxo-2-Piperazineacetic acid

Produkt 1

HCID 113535602-[3-oxo-1-(toluene-4-sulfonyl)-piperazin-2-yl]-N-[6-(1-piperidin-1-ylmethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1(R)-yl]-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a 20 mL flask equipped with stirring was added [3-oxo-1-(toluene-4-sulfonyl)-piperazin-2-yl]-acetic acid (104 mg, 0.33 mmol), 6-(1-piperidin-1-ylmethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1(R)-ylamine (Step g, 90 mg, 0.33 mmol), EDC (Aldrich, 96 mg, 0.50 mmol), HOBt (Aldrich, 45 mg, 0.33 mmol), and CH2Cl2 (2 mL). The reaction mixture was stirred at RT overnight and diluted with CH2Cl2 (50 mL). The organic phase was washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by preparative TLC in 10% MeOH-CH2Cl2 to afford the title compound as a mixture of two diastereomers. MS (ESI): 565 (M+H)+.

Aufarbeitung

  1. customTo a 20 mL flask equipped
  2. stirringThe reaction mixture was stirred at RT overnight
  3. washThe organic phase was washed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by preparative TLC in 10% MeOH-CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-dc67d6ed29cb476d8dc80767b77a3319
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07393852B2

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