Trifluoroacetic acid → (E)-3-(1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)acrylamide

HRID 1880017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1880017
[CH3:1][N:2]([CH2:26][C:27]1[O:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[C:31]=1[CH3:32])[C:3](=[O:25])/[CH:4]=[CH:5]/[C:6]1[CH:24]=[N:23][C:9]2[NH:10][CH2:11][CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][C:8]=2[CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:10]1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15][C:8]2[CH:7]=[C:6](/[CH:5]=[CH:4]/[C:3]([N:2]([CH3:1])[CH2:26][C:27]3[O:28][C:29]4[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=4[C:31]=3[CH3:32])=[O:25])[CH:24]=[N:23][C:9]1=2

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 68412763(E)-tert-butyl 8-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-1,2,3,4-tetrahydropyrido[2,3-b][1,5]diazocine-5(6H)-carboxylate

Produkt 1

HCID 24891659(E)-3-(1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(E)-tert-butyl 8-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-1,2,3,4-tetrahydropyrido[2,3-b][1,5]diazocine-5(6H)-carboxylate (49 mg, 0.1 mmol) was dissolved in 5 mL of DCM followed by the addition of trifluoroacetic acid (5 mL). The solution was stirred for 1.5 h, then concentrated in vacuo, and subjected to prep HPLC purification to obtain the product as a white solid. Yield 25 mg (64%); 1H NMR (400 MHz, CDCl3) δ 10.1 (bs, 1H), 8.01 (m, 2H), 7.50-7.22 (m, 6H), 6.86 (d, J=16.0 Hz, 1H), 4.79 (s, 2H), 4.66 (s, 2H), 3.88 (s, 2H), 3.25 (s, 2H), 3.10 (s, 3H), 2.29 (bs, 5H); ESI MS m/z 391 [C23H26N4O2+H]+

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customHPLC purification

Quellen und Nachweise

ORD-Eintrag
ord-cbc1431d3b6a40a99455a378d0e8cc24
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318720B2

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