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Methyl 2-aminopyridine-4-carboxylate → 3-methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[1,2-a]pyridin-7-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

HRID 50385
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 50385
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11](O)=[O:12])=[CH:10][C:5]2=[N:4][C:3]=1[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1.BrC(C)C(=O)C=CC1C=CC(C#N)=CC=1.NC1C=C(C(OC)=O)C=CN=1.[CH2:50]([O:52][C:53]([CH2:55][CH2:56][NH:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:54])[CH3:51].C(OCC)(=O)C.C(O)C.N>S(Cl)(Cl)=O>[C:58]1([N:57]([CH2:56][CH2:55][C:53]([O:52][CH2:50][CH3:51])=[O:54])[C:11]([C:9]2[CH:8]=[CH:7][N:6]3[C:2]([CH3:1])=[C:3]([CH2:14][CH2:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[CH:20][CH:21]=4)[N:4]=[C:5]3[CH:10]=2)=[O:12])[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1
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Komponenten

7

Edukt 5

HCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 10910393beta-Alanine, N-phenyl-, ethyl esterHCID 184123193-Methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[1,2-a]pyridin-7-yl-carboxylic acidHCID 542928874-Bromo-1-(4-cyanophenyl)-1-penten-3-oneHCID 86587043Ethyl acetate ethanol ammonia

Produkt 1

HCID 18412387
3-methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[1,2-a]pyridin-7-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

1.4 g (4.6 mmol) of 3-methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[1,2-a]pyridin-7-yl-carboxylic acid (prepared from 4-bromo-l-(4-cyanophenyl)-1-penten-3-one and methyl 2-aminopyridine-4-carboxylate analogously to Y. Katsura et al., Chem. Pharm. Bull. 1992, 40, 1424-1438) were suspended in 15 mL of thionyl chloride and heated to boiling for 1 hour until fully dissolved. After the thionyl chloride had been distilled off, the acid chloride was dissolved in 15 mL of pyridine without any further purification and at 0° C. mixed with 1.0 g (5.2 mmol) of N-(2-ethoxycarbonylethyl)aniline. After 1 hour, the solvent was distilled off, the residue was taken up in 30 mL of methylene chloride, washed with 15 mL of 1N hydrochloric acid, and dried with sodium sulfate. After distillation of the solvent and chromatography (silica gel; methylene chloride/ethanol=0 to 2%), a brown oil was obtained. Yield: 1.48 g (64% of theory); Rf value: 0.73 (silica gel; ethyl acetate/ethanol/ammonia=90:10:1).

Aufarbeitung

  1. temperatureheated
  2. dissolutionuntil fully dissolved
  3. distillationAfter the thionyl chloride had been distilled off
  4. dissolutionthe acid chloride was dissolved in 15 mL of pyridine without any further purification and at 0° C.
  5. waitAfter 1 hour
  6. distillationthe solvent was distilled off
  7. washwashed with 15 mL of 1N hydrochloric acid
  8. dry with materialdried with sodium sulfate
  9. distillationAfter distillation of the solvent and chromatography (silica gel; methylene chloride/ethanol=0 to 2%)
  10. customa brown oil was obtained

Quellen und Nachweise

ORD-Eintrag
ord-d8e2acce4bec4d62bba9abbf288ea55d
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06710055B2

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