Hydrochloric Acid → Methyl 6-aminomethyl-10-methyl-phenothiazine-4-acetate hydrochloride

HRID 2395163

Reaktionsgleichung

Reaktionsgleichung von HRID 2395163
C(OC(OCC)C1C=CC=C2C=1SC1C(C=O)=CC=CC=1N2C)C.CS(CSC)=O.C(C1C=CC=C2C=1SC1C(CC(OC)=O)=CC=CC=1N2C)=O.C([O-])(=O)C.[Na+].[ClH:58].NO.[N:61](=[CH:63][C:64]1[CH:77]=[CH:76][CH:75]=[C:74]2[C:65]=1[S:66][C:67]1[C:68]([CH2:79][C:80]([O:82][CH3:83])=[O:81])=[CH:69][CH:70]=[CH:71][C:72]=1[N:73]2[CH3:78])O.Cl>O1CCCC1.CO.[Pd].O>[ClH:58].[NH2:61][CH2:63][C:64]1[CH:77]=[CH:76][CH:75]=[C:74]2[C:65]=1[S:66][C:67]1[C:68]([CH2:79][C:80]([O:82][CH3:83])=[O:81])=[CH:69][CH:70]=[CH:71][C:72]=1[N:73]2[CH3:78]

Komponenten

12

Edukt 7

HCID 313Hydrochloric AcidHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 189724746-Diethoxymethyl-10-methylphenothiazine-4-carbaldehydeHCID 54246440Methyl 6-formyl-10-methyl-phenothiazine-4-acetateHCID 86753153Methyl 6-[(hydroximino)methyl]-10-methyl-phenothiazine-4-acetate

Produkt 1

HCID 67645243Methyl 6-aminomethyl-10-methyl-phenothiazine-4-acetate hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel3×HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 500 mg (1.46 mmol) of 6-diethoxymethyl-10-methyl-phenothiazine-4-carbaldehyde in 5 ml of tetrahydrofuran can be converted analogously to that described in Example 1.1.1.d with 0.22 g (1.75 mmol) of methyl (methylthiomethyl)sulphoxide, 0.14 ml of Triton B solution (35% in methanol) and hydrolysis into methyl 6-formyl-10-methyl-phenothiazine-4-acetate. This compound can be converted analogously to that described in Example 1.1.1.e in methanol, water and tetrahydrofuran using sodium acetate and hydroxylamine hydrochloride into methyl 6-[(hydroximino)methyl]-10-methyl-phenothiazine-4-acetate. This compound can be hydrogenated over palladium/charcaol in methanol and methanolic hydrochloric acid (20%) analogously to that described in Example 1.1.1.f, whereby there is obtained methyl 6-aminomethyl-10-methyl-phenothiazine-4-acetate hydrochloride which can be converted analogously to that described in Example 1.1.2 in dioxan and 1N sodium hydroxide solution using di-tert-butyl dicarbonate into methyl 6-[(1-tert-butylformamido)methyl]-10-methyl-phenothiazine-4-acetate. The product obtained can be hydrolyzed with 1N potassium hydroxide solution in methanol analogously to that described in Example 1.1.3 to give (6-tert-butoxycarbonyl-aminomethyl-10-methyl-phenothiazin-4-yl)-acetic acid prepared according to Example 2.1.1.g.

Quellen und Nachweise

ORD-Eintrag
ord-e1da4e2ea71f4aa4b55caff2383c9def
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811548

Verknüpfte Notizen

Wird geladen…