5-Methoxy[1,3]thiazolo[5,4-b]pyridin-2-amine → N-(5-methoxythiazolo[5,4-b]pyridin-2-yl)-2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-((R)-3-oxocyclopentyl)propionamide

HRID 14993

Reaktionsgleichung

Reaktionsgleichung von HRID 14993
[CH3:1][N:2]1[C:15]2[CH:14]=[C:13]([CH2:16][C:17](OCC)=[O:18])[CH:12]=[CH:11][C:10]=2[S:9](=[O:23])(=[O:22])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.I[CH2:25][C@H:26]1[CH2:34][CH2:33][C:28]2([O:32]CCO2)[CH2:27]1.O=C1CC[C@H](C(OC)=O)C1.[CH3:45][O:46][C:47]1[N:52]=[C:51]2[S:53][C:54]([NH2:56])=[N:55][C:50]2=[CH:49][CH:48]=1>>[CH3:45][O:46][C:47]1[N:52]=[C:51]2[S:53][C:54]([NH:56][C:17](=[O:18])[CH:16]([C:13]3[CH:12]=[CH:11][C:10]4[S:9](=[O:22])(=[O:23])[C:8]5[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=5)[N:2]([CH3:1])[C:15]=4[CH:14]=3)[CH2:25][C@H:26]3[CH2:34][CH2:33][C:28](=[O:32])[CH2:27]3)=[N:55][C:50]2=[CH:49][CH:48]=1

Komponenten

5

Edukt 4

HCID 28015575-Methoxy[1,3]thiazolo[5,4-b]pyridin-2-amineHCID 13827616methyl (1S)-3-oxocyclopentane-1-carboxylateHCID 59340971Ethyl (10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)acetateHCID 67237087(S)-7-iodomethyl-1,4-d ioxaspiro[4.4]nonane

Produkt 1

HCID 86637550N-(5-methoxythiazolo[5,4-b]pyridin-2-yl)-2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-((R)-3-oxocyclopentyl)propionamide

Versuchsvorschrift

Analogously to Example 1 and Example 36, ethyl (10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)acetate, (S)-7-iodomethyl-1,4-d ioxaspiro[4.4]nonane (prepared analogously to Example 40 from commercially available methyl (S)-3-oxo-cyclopentanecarboxylate) and 5-methoxy-thiazolo[5,4-b]pyridin-2-ylamine give N-(5-methoxythiazolo[5,4-b]pyridin-2-yl)-2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-((R)-3-oxocyclopentyl)propionamide.

Quellen und Nachweise

ORD-Eintrag
ord-21acdf692c1a49009e3af8ed3e8a6972
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732440B2

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