1,2-Dichloroethane → HCID 58173379, Verbindung

HRID 2047195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047195
[Br:1][C:2]1[C:3]([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)=[N:4][C:5]2[N:6]([N:9]=[CH:10][C:11]=2[C:12]2[CH:13]=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]=1[NH2:8].C(N(CC)C(C)C)(C)C.[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[C:42](O)=[O:43].C(Cl)CCl>CN(C=O)C>[NH2:8][C:7]1[N:6]2[N:9]=[CH:10][C:11]([C:12]3[CH:13]=[N:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:5]2[N:4]=[C:3]([C:22]2[CH2:23][CH2:24][N:25]([C:42]([C:38]3[S:37][CH:41]=[CH:40][CH:39]=3)=[O:43])[CH2:26][CH:27]=2)[C:2]=1[Br:1]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 107002-Thiophenecarboxylic acidHCID 81531DiisopropylethylamineHCID 66733403HCID 66733403, Verbindung

Produkt 1

HCID 58173379HCID 58173379, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Bromo-3-(quinolin-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine (0.035 mmol) was charged to a 20 mL scintillation vial. Then DMF (1 ml), N,N-diisopropylethylamine (0.14 mmol, 25 μL), thiophene-2-carboxylic acid (0.039 mmol, 5 mg), and EDC (0.039 mmol, 7.4 mg) were added, respectively. The resulting reaction mixture was stirred at room temperature for 18 hours. Upon completion, the reaction mixture was concentrated in vacuo and purified via reverse-phase preparatory HPLC to yield (4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone (m+H=531.06, retention time=3.74 min). Also recovered was the dehalogenated product, (4-(7-amino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone (m+H=453.24, retention time=3.51 min).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. concentrationUpon completion, the reaction mixture was concentrated in vacuo
  3. custompurified via reverse-phase preparatory HPLC

Quellen und Nachweise

ORD-Eintrag
ord-474d1117e90f4f6b8c638282647c9b04
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591943B2

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