p-Toluenesulfonic acid monohydrate → HCID 68686342, Verbindung

HRID 2234279

Reaktionsgleichung

Cl[C:2]1[N:12]=[C:11]2[C:5]([N:6]([CH3:17])[C:7](=[O:16])[CH2:8][CH2:9][N:10]2[CH:13]([CH3:15])[CH3:14])=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:34]=[CH:33][C:22]([C:23]([NH:25][CH:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)=[O:24])=[CH:21][C:20]=1[Cl:35].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)CC(O)C.CO>[Cl:35][C:20]1[CH:21]=[C:22]([CH:33]=[CH:34][C:19]=1[NH:18][C:2]1[N:12]=[C:11]2[C:5](=[CH:4][N:3]=1)[N:6]([CH3:17])[C:7](=[O:16])[CH2:8][CH2:9][N:10]2[CH:13]([CH3:15])[CH3:14])[C:23]([NH:25][CH:26]1[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]1)=[O:24]

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

10-chloro-6-methyl-2-propan-2-yl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one (Intermediate 76, 100 mg, 0.39 mmol) and 4-amino-3-chloro-N-(1-methyl-4-piperidyl)benzamide (Intermediate 79; 127 mg, 0.47 mmol) were suspended in 4-methyl-2-pentanol (3 mL) and p-toluenesulphonic acid monohydrate (74 mg, 0.97 mmol) added. The mixture was heated at 140° C. for 4 hours The mixture was cooled causing a white solid to formed. The whole mixture was diluted with MeOH to give a solution which was absorbed on to an SCX-3 column, washed with methanol and eluted with ammonia/methanol. Concentration and column chromatography (1-2-3-5% NH3 in MeOH/DCM) of the product containing fractions gave the title compound as a white solid (58 mg, 31%).

Aufarbeitung

temperaturewas cooled
customto formed
customto give a solution which
customwas absorbed on to an SCX-3 column
washwashed with methanol
washeluted with ammonia/methanol
concentrationConcentration and column chromatography (1-2-3-5% NH3 in MeOH/DCM) of the product
additioncontaining fractions

Quellen und Nachweise

ORD-Eintrag: ord-6bba51988899447591d18d65a1d297b9
Quelldatensatz: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07709471B2

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