Trifluoroacetic acid → 5-Bromo-3-nitro-4-(4-(1-(pyridin-3-yl)ethyl)piperazin-1-yl)pyridin-2-amine

HRID 416776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 416776
[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.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](C(N2CCN(C(OC(C)(C)C)=O)CC2)C)[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>[Br:1][C:2]1[C:3]([N:12]2[CH2:13][CH2:14][N:15]([CH:18]([C:28]3[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=3)[CH3:19])[CH2:16][CH2:17]2)=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 6422Trifluoroacetic acidHCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amineHCID 578971485-Bromo-3-nitro-4-(4-(1-(pyridin-2-yl)ethyl)piperazin-1-yl)pyridin-2-amineHCID 66622025tert-Butyl 4-(1-(pyridin-3-yl)ethyl)piperazine-1-carboxylate

Produkt 1

HCID 578971265-Bromo-3-nitro-4-(4-(1-(pyridin-3-yl)ethyl)piperazin-1-yl)pyridin-2-amine

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-(1-(pyridin-3-yl)ethyl)piperazine-1-carboxylate (1.1 eq, 0.64 mmol, 186 mg), TFA (2 mL) and CH2Cl2 (2 mL), then 5-bromo-4-chloro-3-nitropyridin-2-amine (147 mg, 0.58 mmol) in iPrOH (3 mL) and DIPEA (1.5 mL). Filtration and washing as previously described gave the product (106 mg, 41% for two steps) as a yellow solid; 1H-NMR (500 MHz, DMSO-d6) 1.33 (d, J=6.7 Hz, 1H, CH3), 3.04 (s, br, 4H, piperazine N(CH2)2), 3.20 (s, br, 4H, piperazine N(CH2)2), 3.59 (q, J=6.8 Hz, 1H, CH), 6.95 (s, br, 2H, NH2), 7.36 (dd, J=7.8, 4.8 Hz, 1H, pyridine H-5), 7.73 (d, br, J=7.8 Hz, 1H, pyridine H-4), 8.14 (s, 1H, bromopyridine H-6), 8.46 (d, br, J=4.7 Hz, 1H, pyridine H-6), 8.52 (s, br, 1H, pyridine H-2);

Aufarbeitung

  1. customThis was prepared
  2. filtrationFiltration
  3. washwashing
  4. customas previously described gave the product (106 mg, 41% for two steps) as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-8cafb450e2ef4068995369615c37a99f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088761B2

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