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1-Hydroxybenzotriazole → HCID 21984036, Verbindung

HRID 1818242
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1818242
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][O:5][CH:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:45][CH2:46][CH2:47][CH2:48][CH2:49][N:50]1[C:62]2[C:61]3[CH:60]=[CH:59][C:58]([C:63]4[CH:64]=[N:65][CH:66]=[CH:67][CH:68]=4)=[CH:57][C:56]=3[N:55]=[C:54]([NH2:69])[C:53]=2[N:52]=[C:51]1[CH2:70][O:71][CH2:72][CH3:73]>C(Cl)(Cl)Cl.CC(N(C)C)=O>[NH2:69][C:54]1[C:53]2[N:52]=[C:51]([CH2:70][O:71][CH2:72][CH3:73])[N:50]([CH2:49][CH2:48][CH2:47][CH2:46][NH:45][C:11](=[O:12])[C:10]3[CH:9]=[CH:8][C:7]([CH:6]([O:5][CH2:4][CH2:3][N:2]([CH3:22])[CH3:1])[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:15][CH:14]=3)[C:62]=2[C:61]2[CH:60]=[CH:59][C:58]([C:63]3[CH:64]=[N:65][CH:66]=[CH:67][CH:68]=3)=[CH:57][C:56]=2[N:55]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15453776HCID 15453776, VerbindungHCID 672820741-(4-aminobutyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 21984036HCID 21984036, VerbindungAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 4-[(2-dimethylaminoethoxy)phenylmethyl]benzoic acid (0.433 g) and 1-hydroxybenzotriazole (0.196 g) in chloroform (7 mL) was cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.277 g) was added in small portions over a 2 minute period. The mixture was stirred for 1 hour and then added dropwise to a chilled (0° C.) solution of 1-(4-aminobutyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (0.400 g) in anhydrous dimethylacetamide (7 mL). The cooling bath was removed and the reaction was stirred for an additional 16 hours. Water was added and the mixture was made acidic by the addition of 4N hydrochloric acid. The aqueous fraction was extracted with diethyl ether (3×) to remove the dimethylacetamide. Sodium hydroxide (10% in water) was added to make the aqueous fraction basic and the aqueous fraction was subsequently extracted with multiple portions of dichloromethane. The organic fractions were combined, washed sequentially with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using a gradient of CMA/chloroform as the eluent. A final recrystallization from acetonitrile provided 0.426 g of N-[4-(4-amino-2-ethoxymethyl-7-(pyridin-3-yl)imidazo[4,5-c]quinolin-1-yl)butyl]-4-[(2-dimethylaminoethoxy)phenylmethyl]benzamide as a white crystalline solid, mp 157.0-161.0° C.

Aufarbeitung

  1. additionadded dropwise to
  2. customThe cooling bath was removed
  3. stirringthe reaction was stirred for an additional 16 hours
  4. additionWater was added
  5. additionthe mixture was made acidic by the addition of 4N hydrochloric acid
  6. extractionThe aqueous fraction was extracted with diethyl ether (3×)
  7. customto remove the dimethylacetamide
  8. additionSodium hydroxide (10% in water) was added
  9. extractionthe aqueous fraction was subsequently extracted with multiple portions of dichloromethane
  10. washwashed sequentially with water and brine
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by flash column chromatography
  15. customA final recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-e5c063c9e52d4a999c911882f1301273
Quelldatensatz
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07598382B2

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