Pyridine → (6S-cis)-methyl [2-chloro-4-fluoro-5-(6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)phenyl][(chloromethyl)sulfonyl]carbamate

HRID 1107255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1107255
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[C:11]([N:13]2[C:17](=[O:18])[C@H:16]3[CH2:19][C@H:20]([F:22])[CH2:21][N:15]3[C:14]2=[O:23])[C:10]([F:24])=[CH:9][C:8]=1[Cl:25])(=[O:5])=[O:4].N1C=CC=CC=1.Cl[C:33]([O:35][CH3:36])=[O:34]>ClCCl>[Cl:25][C:8]1[CH:9]=[C:10]([F:24])[C:11]([N:13]2[C:17](=[O:18])[C@H:16]3[CH2:19][C@H:20]([F:22])[CH2:21][N:15]3[C:14]2=[O:23])=[CH:12][C:7]=1[N:6]([S:3]([CH2:2][Cl:1])(=[O:5])=[O:4])[C:33](=[O:34])[O:35][CH3:36]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 11037075Profluazol

Produkt 1

HCID 70275299(6S-cis)-methyl [2-chloro-4-fluoro-5-(6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)phenyl][(chloromethyl)sulfonyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of the title compound of Example 1, Step H (0.32 g, 0.7 mmol) and pyridine (0.5 mL) in dichloromethane (5 mL) was added a solution of methyl chloroformate (0.09 g, 0.95 mmol) in dichloromethane (1 mL) at room temperature. After completion of the reaction (2 h), the solvents were removed in vacuo and the title compound of Step A, a compound of this invention, was isolated by flash chromatography (0.31 g, 95%) as a white solid melting at 108-115° C. 1H NMR (CDCl3) δ 7.40 (m, 2H), 5.42 (m, 1H), 5.36 (dd, 1H), 4.92 (dd, 1H), 4.60 (m, 1H), 4.04 (m, 1H), 3.82 (s, 3H), 3.60 (dd, 1H), 2.64 (m, 1H), 2.02 (m, 1H).

Aufarbeitung

  1. customAfter completion of the reaction (2 h)
  2. customthe solvents were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-05fdbf6b01854db1953373827cb43ab7
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06060432

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