Ethyl Acetate → 1-[bis(4-chlorophenyl)methyl]-3-{(methylsulfonyl)[(N-4-methylpiperazinylcarbamoyl)phenyl]methylene}azetidine

HRID 25190

Reaktionsgleichung

Reaktionsgleichung von HRID 25190
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:46]2[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=2)[N:17]2[CH2:20][C:19](=[C:21]([S:42]([CH3:45])(=[O:44])=[O:43])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24](C(OC4C(F)=C(F)C(F)=C(F)C=4F)=O)[CH:23]=3)[CH2:18]2)=[CH:12][CH:11]=1.[C:53](OCC)(=[O:55])C>CN(C)C=O>[Cl:52][C:49]1[CH:48]=[CH:47][C:46]([CH:16]([C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)[N:17]2[CH2:18][C:19](=[C:21]([S:42]([CH3:45])(=[O:44])=[O:43])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[C:53](=[O:55])[NH:1][N:2]3[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]3)[CH2:20]2)=[CH:51][CH:50]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 813491-Amino-4-methylpiperazineHCID 225653571-[Bis(4-chlorophenyl)methyl]-3-{(methylsulfonyl)[3-(pentafluorophenoxycarbonyl)phenyl]methylene]azetidine

Produkt 1

HCID 225653131-[bis(4-chlorophenyl)methyl]-3-{(methylsulfonyl)[(N-4-methylpiperazinylcarbamoyl)phenyl]methylene}azetidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.083 g of 1-amino-4-methylpiperazine is added to a solution of 0.45 g of 1-[bis(4-chlorophenyl)methyl]-3-{(methylsulfonyl)[3-(pentafluorophenoxycarbonyl)phenyl]methylene]azetidine in 5 cm3 of dimethylformamide. The mixture is stirred for 20 hours at room temperature and then 40 cm3 of ethyl acetate are added. The organic phase is washed with 4 times 20 cm3 of water, dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is triturated with 10 cm3 of ethyl ether, filtered and then dried. 0.2 g of 1-[bis(4-chlorophenyl)methyl]-3-{(methylsulfonyl)[(N-4-methylpiperazinylcarbamoyl)phenyl]methylene}azetidine is obtained in the form of a yellow solid melting at 162° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 2.20 (3H, s, NCH3), 2.40 (4H, m, 2 NCH2), 2.90 (4H, m, 2 NCH2), 2.95 (3H, s, SCH3), 3.80 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.80 (1H, s, NCH), 7.40 (4H, d, J=7 Hz, 4CH arom.), 7.50 (4H, d, J=7 Hz, 4CH arom.), 7.55 (2H, m, 2CH arom.), 7.80 (2H, m, 2CH arom.), 9.50 (1H, s, CONH)].

Aufarbeitung

  1. washThe organic phase is washed with 4 times 20 cm3 of water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is triturated with 10 cm3 of ethyl ether
  5. filtrationfiltered
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-91dce75ce8af4f40af4523c96b9a9564
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858603B2

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