p-Toluenesulfonic acid monohydrate → N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxyprop-1-ynyl)-1-methyl-1H-thieno[2,3-c][1,2]thiazine-3-carboxamide 2,2-Dioxide

HRID 411218Notes

Reaction equation

[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:15](=[O:17])(=[O:16])[N:14]([CH3:18])[C:13]3[S:19][C:20]([C:22]#[C:23][CH2:24][O:25]C4CCCCO4)=[CH:21][C:12]=3[C:11]=2[OH:32])=[O:9])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:15](=[O:16])(=[O:17])[N:14]([CH3:18])[C:13]3[S:19][C:20]([C:22]#[C:23][CH2:24][OH:25])=[CH:21][C:12]=3[C:11]=2[OH:32])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirring suspension of 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 (Preparation 36, 0.20 g) in MeOH (20 mL) at ambient temperature is added p-toluenesulfonic acid monohydrate (0.030 g). The resulting solution is heated at 60° C. for 45 min. The mixture is cooled to 0° C. and the resulting solid is filtered to afford 0.087g (52%) of the title compound as a white solid. Physical characteristics; 1H NMR (DMSO-d6) δ 3.44, 4.30, 4.48, 7.35, 7.37, 8.50; IR (diffuse reflectance) 3354, 1618, 1570, 1538, 1493, 1436, 1367, 1351, 1304, 1291, 1189, 1151, 1092, 1015, 815 cm−1; MS (EI) m/z 438 (M+). Anal. Found: C, 49.23; H, 3.49; N, 6.38.

Workup

temperatureThe mixture is cooled to 0° C.
filtrationthe resulting solid is filtered

Sources & evidence

ORD record: ord-c5c27996613d472bb6624f7bb41c2695
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559145B2

Reaction notes

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