p-Toluenesulfonic acid monohydrate → N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-1-methyl-1H-2,1-benzothiazine-3-carboxamide 2,2-Dioxide

HRID 411234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 411234
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:11](=[O:33])(=[O:32])[N:12]([CH3:31])[C:13]3[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH2:23][O:24]C4CCCCO4)=[CH:17][C:14]=3[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:11](=[O:33])(=[O:32])[N:12]([CH3:31])[C:13]3[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH2:23][OH:24])=[CH:17][C:14]=3[C:15]=2[OH:16])=[O:9])=[CH:34][CH:35]=1

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 69732527N-(4-Chlorobenzyl)4-hydroxy-1-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)-1-propynyl)-1H-2,1-benzothiazine-3-carboxamide 2,2-Dioxide

Produkt 1

HCID 54676519N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-1-methyl-1H-2,1-benzothiazine-3-carboxamide 2,2-DioxideAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of N-(4-chlorobenzyl)-4-hydroxy-1-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)-1-propynyl)-1H-2,1-benzothiazine-3-carboxamide 2,2-dioxide (Preparation 53, 0.30 g) in CH3OH (30 mL) is added p-TsOH.H2O (30 mg). The reaction mixture is heated to 55° C. for 2 h. The solvent is evaporated in vacuo and the residue is diluted with Et2O (20 mL) and sonicated. The resulting precipitate is filtered and washed with Et2O to afford 0.16 g (61%) of the title compound as a white solid. Physical characteristics: m.p. 167-168° C.; 1H NMR (300 MHz, CDCl3) δ 15.82, 8.21, 7.93, 7.69, 7.36, 7.17, 4.60, 4.53, 3.49, 2.21; IR (diffuse reflectance) 3344, 1615, 1579, 1554, 1540, 1490, 1392, 1385, 1325, 1310, 1293, 1279, 1160, 1093, 1031 cm−1; MS (ESI+) m/z 433 (MH+); HRMS (FAB) m/z 433.0614 (C20H17ClN2O5S+H). Anal. Found: C, 54.57; H, 4.16; N, 6.10.

Aufarbeitung

  1. customThe solvent is evaporated in vacuo
  2. additionthe residue is diluted with Et2O (20 mL)
  3. customsonicated
  4. filtrationThe resulting precipitate is filtered
  5. washwashed with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-3cf9f525b648497a8a3a696b92d8ea65
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559145B2

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