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Triethylamine → N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-methylpropanamide

HRID 11369
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 11369
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].Cl.[NH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:18]([CH3:20])=[C:17]([CH3:21])[N:16]=[C:15]([NH2:22])[C:14]=2[N:13]=[C:12]1[CH3:23].NCCN1C2C(C)=C(C)N=C(N)C=2N=C1C.C(N(CC)CC)C>ClCCl>[NH2:22][C:15]1[C:14]2[N:13]=[C:12]([CH3:23])[N:11]([CH2:10][CH2:9][NH:8][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[C:19]=2[C:18]([CH3:20])=[C:17]([CH3:21])[N:16]=1
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Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 219738191-(2-aminoethyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochlorideHCID 219738201-(2-aminoethyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Produkt 1

HCID 10236412N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-methylpropanamide
Ausbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Isobutyryl chloride (1.3 mL, 12.2 mmol) was added dropwise to a mixture of 1-(2-aminoethyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride (4.0 g of material from Example 24, 12.2 mmol), triethylamine (85 mL, 610 mmol) and dichloromethane (400 mL). After 15 minutes analysis by high performance liquid chromatography indicated that the reaction was complete. The solvents were removed under reduced pressure. The residue was partitioned between chloroform (250 mL) and water (250 mL) containing 10 g of sodium carbonate (pH 12). This mixture was placed in a continuous extractor and extracted with chloroform for 24 hours. The extract was dried over magnesium sulfate and then concentrated under reduced pressure to provide a light yellow oil. The oil was purified by chromatography (silica gel eluting with 85/15 dichloromethane/methanol) to provide 2.63 g of N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-methylpropanamide as a white powder, m.p. 220–222° C.

Aufarbeitung

  1. customThe solvents were removed under reduced pressure
  2. customThe residue was partitioned between chloroform (250 mL) and water (250 mL)
  3. additioncontaining 10 g of sodium carbonate (pH 12)
  4. extractionextracted with chloroform for 24 hours
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto provide a light yellow oil
  8. customThe oil was purified by chromatography (silica gel eluting with 85/15 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-8381eaf7159647cbafadef6b071a8849
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07098221B2

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