Hydroxyamine hydrochloride → HCID 136343918, Verbindung

HRID 1012940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012940
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([C@H:14]3[O:19][CH2:18][C@H:17]([NH:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]5[S:26][CH2:27][C:28](=[O:32])[NH:29][C:30]=5[N:31]=4)[CH2:16][CH2:15]3)=O)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.[NH2:34][OH:35]>N1C=CC=CC=1>[OH:35][N:34]=[C:12]([C:10]1[S:11][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=2[N:9]=1)[C@H:14]1[O:19][CH2:18][C@H:17]([NH:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[S:26][CH2:27][C:28](=[O:32])[NH:29][C:30]=3[N:31]=2)[CH2:16][CH2:15]1

Komponenten

4

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 11998933HCID 11998933, Verbindung

Produkt 1

HCID 136343918HCID 136343918, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of (3R,6S)-6-{[6-(4-methoxy-benzothiazole-2-carbonyl)-tetrahydro-pyran-3-ylamino]-methyl}-4H-pyrido[3,2-b][1,4]thiazin-3-one (Example 29, 47 mg, 0.1 mmol), and hydroxylamine hydrochloride (5 eq) in pyridine (1 ml) was stirred at RT overnight. The mixture was concentrated in vacuo and partitioned between NH4OH and DCM. The organic layers were dried over MgSO4 and concentrated. Chromatography on SiO2 (EtOAc/MeOH 9:1 +1% NH4OH) gave the title compound as yellow solid (10 mg, 20%).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between NH4OH and DCM
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-14a4a5ba7e4f4df58c93aa68e586d69a
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981886B2

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