Trifluoroacetic acid → 5-Bromo-4-(4-((6-methoxypyridin-3-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine

HRID 416850

Reaktionsgleichung

Reaktionsgleichung von HRID 416850
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH:18](C3C=CC=CN=3)C)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:26][O:27][C:28]1[N:33]=[CH:32][C:31](CN2CCN(C(OC(C)(C)C)=O)CC2)=[CH:30][CH:29]=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[CH2:17][CH2:16][N:15]([CH2:18][C:31]3[CH:32]=[N:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)[CH2:14][CH2:13]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 57897155tert-Butyl 4-((6-methoxypyridin-3-yl)methyl)piperazine-1-carboxylate

Produkt 1

HCID 578971545-Bromo-4-(4-((6-methoxypyridin-3-yl)methyl)piperazin-1-yl)-3-nitropyridin-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-((6-methoxypyridin-3-yl)methyl)piperazine-1-carboxylate (1.1 eq, 0.54 mmol, 165 mg), TFA (1 mL) and CH2Cl2 (3 mL), then 5-bromo-4-chloro-3-nitropyridin-2-amine (123 mg, 0.49 mmol) in iPrOH (3.5 mL) and DIPEA (1 mL). Filtration and washing as previously described gave the product (89 mg, 40% for two steps) as a yellow solid; δH (500 MHz, DMSO-d6) 2.50 (hidden by DMSO peak, s, br, 4H, piperazine N(CH2)2), 3.05 (s, br, 4H, piperazine N(CH2)2), 3.48 (s, 2H, NCH2), 3.84 (s, 3H, OCH3), 6.80 (d, J=8.5 Hz, 1H, pyridine H-5), 6.98 (s, br, 2H, NH2), 7.66 (dd, J=8.5, 2.3 Hz, 1H, pyridine H-4), 8.07 (d, J=1.1 Hz, 1H, pyridine H-2), 8.16 (s, 1H, bromopyridine H-6); LC (Method B)-MS (ESI, m/z): Rt=2.33 min—423, 425 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 423.0777, calculated for C16H19BrN6O3 (M+H)+: 423.0780.

Aufarbeitung

  1. customThis was prepared
  2. filtrationFiltration
  3. washwashing
  4. customas previously described gave the product (89 mg, 40% for two steps) as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-a49a3119ae6943558af658439b89ce76
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088761B2

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