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

HRID 1058796

Reaktionsgleichung

Reaktionsgleichung von HRID 1058796
[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-d76dd840ece04949b4952e397ab168a2
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518264B2

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