p-Toluenesulfonic acid monohydrate → 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

HRID 1914611

Reaktionsgleichung

[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)=[N:5][N:4]=[N:3]1.[NH2:15][O:16][CH2:17][C:18]1[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][CH:19]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)C.ClCCl>[CH3:1][N:2]1[C:6]([C:7](=[N:15][O:16][CH2:17][C:18]2[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][CH:19]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:4]=[N:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

Under protective gas (argon), a reaction tube containing a solution of (1-methyl-1H-tetrazol-5-yl)(phenyl)methanone (188 mg; 1.0 mmol), 6-[(aminooxy)methyl]pyridin-2-amine (139 mg; 1.0 mmol) and p-toluenesulfonic acid monohydrate (190 mg; 1.0 mmol) in 2-propanol (2 mL) is sealed and heated in a microwave oven at 160° C. for 90 min. For workup, the mixture is allowed to cool down, diluted with dichloromethane (10 mL) and washed twice with 3 ml each time of sat. aq. sodium bicarbonate. The aqueous phase is extracted with dichloromethane and the combined organic layers dried over magnesium sulfate and concentrated under reduced pressure. Purification on silica gel affords 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine as a colourless oil [205 mg; 66% of theory; HPLC/MS: m/z=310 (M+H); log P(HCOOH)=1.13].

Aufarbeitung

customis sealed
temperatureto cool down
washwashed twice with 3 ml each time of sat. aq. sodium bicarbonate
extractionThe aqueous phase is extracted with dichloromethane
dry with materialthe combined organic layers dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customPurification on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-c6461ee42459420a99264da3e879168d
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08614217B2

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