Triethylamine → N-(4-Chlorobenzyl)4-hydroxy-1-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)-1H-thieno[2,3-c][1,2]thiazine-3-carboxamide 2,2-Dioxide

HRID 1070633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070633
[CH3:1][N:2]1[C:7]2[S:8][C:9]([C:11]#[C:12][CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)=[CH:10][C:6]=2[C:5](=[O:21])[CH2:4][S:3]1(=[O:23])=[O:22].C(N(CC)CC)C.[Cl:31][C:32]1[CH:41]=[CH:40][C:35]([CH2:36][N:37]=[C:38]=[O:39])=[CH:34][CH:33]=1>CS(C)=O.Cl>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([CH2:36][NH:37][C:38]([C:4]2[S:3](=[O:22])(=[O:23])[N:2]([CH3:1])[C:7]3[S:8][C:9]([C:11]#[C:12][CH2:13][O:14][CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][O:16]4)=[CH:10][C:6]=3[C:5]=2[OH:21])=[O:39])=[CH:40][CH:41]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 33723791-Chloro-4-(isocyanatomethyl)benzeneHCID 223972121-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide

Produkt 1

HCID 69731037N-(4-Chlorobenzyl)4-hydroxy-1-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)-1H-thieno[2,3-c][1,2]thiazine-3-carboxamide 2,2-DioxideAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a stirring solution of 1-methyl-6-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)-1H-thieno[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide (Preparation 35, 0.64 g) and triethylamine (0.27 g) in DMSO (15 mL) at ambient temperature is added 4-chloro-benzylisocyanate (0.45 g). The resulting red solution is stirred overnight at ambient temperature and diluted with 10% aqueous HCl (20 mL). The aqueous layer is extracted with EtOAc (3×25 ml). The combined organic layers are dried over MgSO4 and concentrated in vacuo. The residue is dissolved in EtOAc (15 mL) and allowed to stand at ambient temperature overnight. The resulting solid is collected by filtration, washed with EtOAc (10 ml) and dried in vacuo at 50° C. to afford 0.29 g (31%) of the title compound as a tan solid. Physical characteristics: 1H NMR (CDCl3) δ1.58-1.82, 3.49, 3.60, 3.89, 4.50, 4.56, 4.86, 7.30, 7.42, 7.71, 15.62; IR (diffuse reflectance) 3353, 2945, 1615, 1581, 1541, 1493, 1431, 1366, 1345, 1308, 1296, 1276, 1183, 1119, 1031 cm−1; MS (EI) m/z 522 (M+). Anal. Found: C, 53.17; H, 4.49; N, 5.67.

Aufarbeitung

  1. extractionThe aqueous layer is extracted with EtOAc (3×25 ml)
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in EtOAc (15 mL)
  5. waitto stand at ambient temperature overnight
  6. filtrationThe resulting solid is collected by filtration
  7. washwashed with EtOAc (10 ml)
  8. customdried in vacuo at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-abc1fc67e7ea4ed89ac4605e21a78e91
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903097B2

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