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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 1070634
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HRID 1070634 반응식
[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
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4

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HCID 521998p-Toluenesulfonic acid monohydrateHCID 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-Dioxide

생성물 1

HCID 54676514N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxyprop-1-ynyl)-1-methyl-1H-thieno[2,3-c][1,2]thiazine-3-carboxamide 2,2-Dioxide수율 52%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

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 0.087 g (52%) of the title compound as a white solid. Physical characteristics; 1H NMR (DMSO-d6) δ3.44, 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.

후처리

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

출처 및 근거

ORD 기록
ord-13cf8d3eef2c41e8aeba468342b240d5
출처 데이터셋
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06903097B2

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