Trifluoroacetic acid → 1-(2-(4-(2-Amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)ethyl)-3-phenylurea

HRID 416759

Reaktionsgleichung

Reaktionsgleichung von HRID 416759
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH:18](C3C=CC=CN=3)[CH3:19])[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:26]1([NH:32][C:33](=[O:50])[NH:34]CCN2CCN(C(OC(C)(C)C)=O)CC2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O)(C(F)(F)F)=O.BrC1C(Cl)=C([N+]([O-])=O)C(N)=NC=1>CC(O)C.CCN(C(C)C)C(C)C.C(Cl)Cl>[NH2:8][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][NH:34][C:33]([NH:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:50])[CH2:14][CH2:13]2)[C:2]([Br:1])=[CH:7][N:6]=1

Komponenten

8

Edukt 4

HCID 6422Trifluoroacetic acidHCID 2822252Tert-butyl 4-(2-(3-phenylureido)ethyl)piperazine-1-carboxylateHCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amineHCID 578971485-Bromo-3-nitro-4-(4-(1-(pyridin-2-yl)ethyl)piperazin-1-yl)pyridin-2-amine

Produkt 1

HCID 578972931-(2-(4-(2-Amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)ethyl)-3-phenylurea

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3776IsopropanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

This was prepared using the same procedure as for 5-bromo-3-nitro-4-(4-(1-(pyridin-2-yl)ethyl)piperazin-1-yl)pyridin-2-amine, but here using tert-butyl 4-(2-(3-phenylureido)ethyl)piperazine-1-carboxylate (1.1 eq, 0.43 mmol, 150 mg), TFA (1 mL) and CH2Cl2 (2 mL), then 5-bromo-4-chloro-3-nitropyridin-2-amine (103 mg, 0.29 mmol) in iPrOH (2 mL) and DIPEA (0.5 mL). Filtration and washing as previously described gave the product (190 mg, 95% for two steps) as a bright yellow solid; 1H-NMR (500 MHz, DMSO-d6) 2.45-2.65 (2 m, 4H, piperazine N(CH2)2), 3.08-3.17 (2 m, 6H, piperazine N(CH2)2 & CH2), 3.60-3.63 (m, 2H, CH2), 6.10 (br s, 1H, NH), 6.89 (t, J=6.9 Hz, 1H, phenyl H-4), 7.02 (br s, 2H, NH2), 7.21 (t, br, J=7.4 Hz, 2H, phenyl H-3 & H-5), 7.38 (d, J=7.5 Hz, 2H, phenyl H-2 & H-6), 8.17 (s, 1H, pyridine H-6), 8.66 (s, br, 1H, NH);

Aufarbeitung

  1. customThis was prepared
  2. filtrationFiltration
  3. washwashing
  4. customas previously described gave the product (190 mg, 95% for two steps) as a bright yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-86bba63900b346a185126c89f369efd4
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088761B2

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