2H-1,2,4-Benzothiadiazine-3-acetic acid ethyl ester 1,1-dioxide → 4-[(2-Chloro-1,3-thiazol-5-yl)methyl]-6-{1,1-dioxido-7-[(triisopropylsilyl)oxy]-4H-1,2,4-benzothiadiazin-3-yl}-7-hydroxythieno[3,2-b]pyridin-5(4H)-one

HRID 601291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601291
[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]2[C:13]3[CH:14]=[CH:15][S:16][C:12]=3[C:11](=[O:17])O[C:9]2=[O:18])=[CH:5][N:6]=1.C(N1C2N=CC=CC=2C(=O)OC1=O)CCC.[O:35]=[S:36]1(=[O:63])[C:41]2[CH:42]=[C:43]([O:46][Si:47]([CH:54]([CH3:56])[CH3:55])([CH:51]([CH3:53])[CH3:52])[CH:48]([CH3:50])[CH3:49])[CH:44]=[CH:45][C:40]=2[NH:39][C:38]([CH2:57]C(OCC)=O)=[N:37]1.O=S1(=O)C2C=CC=CC=2NC(CC(OCC)=O)=N1>>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]2[C:9](=[O:18])[C:57]([C:38]3[NH:39][C:40]4[CH:45]=[CH:44][C:43]([O:46][Si:47]([CH:51]([CH3:53])[CH3:52])([CH:54]([CH3:55])[CH3:56])[CH:48]([CH3:49])[CH3:50])=[CH:42][C:41]=4[S:36](=[O:63])(=[O:35])[N:37]=3)=[C:11]([OH:17])[C:12]3[S:16][CH:15]=[CH:14][C:13]2=3)=[CH:5][N:6]=1

Komponenten

5

Edukt 4

HCID 6588352H-1,2,4-Benzothiadiazine-3-acetic acid ethyl ester 1,1-dioxideHCID 103985421-butyl-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dioneHCID 865921511-[(2-chloro-1,3-thiazol-5-yl)methyl]-2H-thieno[3,2-d][1,3]oxazine-2,4(1H)-dioneHCID 86592152Ethyl {1,1-dioxido-7-[(triisopropylsilyl)oxy]-4H-1,2,4-benzothiadiazin-3-yl}acetate

Produkt 1

HCID 1363739914-[(2-Chloro-1,3-thiazol-5-yl)methyl]-6-{1,1-dioxido-7-[(triisopropylsilyl)oxy]-4H-1,2,4-benzothiadiazin-3-yl}-7-hydroxythieno[3,2-b]pyridin-5(4H)-one

Versuchsvorschrift

The title compound was prepared according to the procedure of Example 1D substituting the product of Example 140A for the product of Example 1B and substituting the product of Example 307C for the product of Example 1C (0.29 g, 66%). MS (ESI−) m/z 649 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.09 (d, J=7.35 Hz, 18 H) 1.28 (m, 3 H) 5.63 (s, 2 H) 7.22 (d, J=2.57 Hz, 1 H) 7.31 (dd, J=8.82, 2.94 Hz, 1 H) 7.65 (d, J=8.82 Hz, 1 H) 7.86 (d, J=5.52 Hz, 1 H) 7.95 (s, 1 H) 8.42 (d, J=5.52 Hz, 1 H) 14.05 (s, 1 H) 14.96 (s, 1 H).

Quellen und Nachweise

ORD-Eintrag
ord-21dec6eb81a14713be3157ebbc3c3738
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902203B2

Notizen zur Reaktion

Wird geladen…