Trifluoroacetic acid → HCID 53794364, Verbindung

HRID 1432959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432959
Cl.Cl.[NH2:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][C:16]3=[O:21])=[CH:11][CH:12]=2)[N:7]=[CH:6][N:5]=1.Br[CH2:23][C:24]1[S:28][C:27]2[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:26]=2[CH:25]=1.C([O-])([O-])=O.[K+].[K+].FC(F)(F)C(O)=O>CN(C=O)C.O>[NH2:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][N:15]3[CH2:20][CH2:19][N:18]([CH2:23][C:24]4[S:28][C:27]5[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:26]=5[CH:25]=4)[CH2:17][C:16]3=[O:21])=[CH:11][CH:12]=2)[N:7]=[CH:6][N:5]=1

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 22394336HCID 22394336, VerbindungHCID 690243421-(4-Aminoquinazoline-7-ylmethyl)piperazine-2-one bishydrochloride

Produkt 1

HCID 53794364HCID 53794364, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-aminoquinazoline-7-ylmethyl)piperazine-2-one bishydrochloride (1.84 g, 5.73 mmol), EXAMPLE 72, in DMF (20 mL) is added 2-bromomethyl-6-chloro-benzo[b]thiophene, EXAMPLE 5, (1.5 g, 5.73 mmol) and K2CO3 (4.0 g, 28.7 mmol). The solution is stirred for 16 hours. After this time, the solution is diluted with water. The solution is acidified with trifluoroacetic acid. The product is purified by RP-HPLC eluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 50% CH3CN/H2O (0.1% TFA). The appropriate collected fractions are lyopholized to afford the title compound as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ9.78 (bs, 3H), 8.82 (s, 1H), 8.34 (d, 1H), 8.07 (s, 1H), 7.81 (d, 1H), 7.63 (d, 1H), 7.51 (s, 1H), 7.32 (m, 2H), 4.71 (s, 2H), 3.95 (s, 2H), 3.28 (m, 4H), 2.80 (m, 2H).

Aufarbeitung

  1. customThe product is purified by RP-HPLC
  2. washeluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 50% CH3CN/H2O (0.1% TFA)
  3. customThe appropriate collected fractions

Quellen und Nachweise

ORD-Eintrag
ord-d1f7f230aedc41d0bb697d74b7e3ffc2
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

Notizen zur Reaktion

Wird geladen…