1,2-Dichloroethane → HCID 57819877, Verbindung

HRID 657422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657422
[NH2:1][CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[N:7][C:6]2[N:11]([CH2:14][CH3:15])[N:12]=[CH:13][C:5]=2[C:4]=1[NH:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[CH3:23][C:24]([CH3:32])([CH2:28][C:29]([OH:31])=[O:30])[C:25]([OH:27])=[O:26].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[CH2:14]([N:11]1[C:6]2=[N:7][C:8]([CH2:9][CH3:10])=[C:3]([CH2:2][NH:1][C:29](=[O:30])[CH2:28][C:24]([CH3:32])([CH3:23])[C:25]([OH:27])=[O:26])[C:4]([NH:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:5]2[CH:13]=[N:12]1)[CH3:15].[CH2:14]([N:11]1[C:6]2=[N:7][C:8]([CH2:9][CH3:10])=[C:3]([CH2:2][NH:1][C:25](=[O:26])[C:24]([CH3:32])([CH3:23])[CH2:28][C:29]([OH:31])=[O:30])[C:4]([NH:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:5]2[CH:13]=[N:12]1)[CH3:15]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 117012,2-Dimethylsuccinic acidHCID 757711-HydroxybenzotriazoleHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Produkt 2

HCID 57819877HCID 57819877, VerbindungAusbeute 55,6 %HCID 57819884HCID 57819884, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

174(a) 5-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (303.0 mg, 1.0 mmol) and 2,2-dimethylbutanedioic acid (146.0 mg, 1.0 mmol) were dissolved in DCM (10 mL), followed by the addition of HOBt (1.0 eq, 153.0 mg) and EDC (1.0 eq, 192.0 mg). The resultant solution was stirred overnight. The solution was purified by reverse phase HPLC using a Gilson to yield 4-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-2,2-dimethyl-4-oxobutanoic acid and 4-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3,3-dimethyl-4-oxobutanoic acid mixture 120 mg.

Aufarbeitung

  1. customThe solution was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f64c5c6dd2034cfeb4dd8e52ee18202d
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071588B2

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