Triethylamine → 1-[(3S)-4-[(3-cyano-1-naphthoyl)(methyl)amino]-3-(3,4-dichlorophenyl)butyl)azetidin-3-yl methanesulfonate

HRID 749440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749440
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][C@H:18]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:19][CH2:20][N:21]2[CH2:24][CH:23]([OH:25])[CH2:22]2)[CH3:16])=[O:14])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C(Cl)Cl>[CH3:41][S:42]([O:25][CH:23]1[CH2:24][N:21]([CH2:20][CH2:19][C@@H:18]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:17][N:15]([C:13]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:14])[CH3:16])[CH2:22]1)(=[O:44])=[O:43]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 689772843-cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-(3-hydroxyazetidin-1-yl)butyl]-N-methyl-1-naphthamide

Produkt 1

HCID 586835281-[(3S)-4-[(3-cyano-1-naphthoyl)(methyl)amino]-3-(3,4-dichlorophenyl)butyl)azetidin-3-yl methanesulfonateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3-Cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-(3-hydroxyazetidin-1-yl)butyl]-N-methyl-1-naphthamide (0.20 g, 0.41 mmol) was dissolved in CH2Cl2 and to the resultant solution was added triethylamine (0.17 mL, 0.41 mmol). The mixture was cooled to 0° C. before careful addition of methanesulfonyl chloride (0.03 mL, 0.41 mmol). The mixture was stirred with cooling for 30 min and then at room temperature for 1 h. The reaction mixture was diluted with CH2Cl2 and then washed with hydrochloric acid (1M), saturated NaHCO3 and then with brine. The organic solution was dried over MgSO4 and the solvent removed by evaporation. There was obtained 0.21 g (92%) of 1-[(3S)-4-[(3-cyano-1-naphthoyl)(methyl)amino]-3-(3,4-dichlorophenyl)butyl]azetidin-3-yl methanesulfonate as a solid. LCMS: m/z 560 (M+)+.

Aufarbeitung

  1. temperaturewith cooling for 30 min
  2. washwashed with hydrochloric acid (1M), saturated NaHCO3
  3. dry with materialThe organic solution was dried over MgSO4
  4. customthe solvent removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-76a8e6a12702426abb51122c24dd523a
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402581B2

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