Triethylamine → tert-butyl {4-[7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}carbamate

HRID 598279

Reaktionsgleichung

Reaktionsgleichung von HRID 598279
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[CH2:30]([O:37][C:38]1[CH:47]=[C:46]2[C:41]([C:42]([NH:49][CH2:50][CH2:51][O:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[C:43]([NH2:48])[CH:44]=[N:45]2)=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClC(Cl)C.CN(C)C1C=CN=CC=1.C(OCC)C>[CH2:30]([O:37][C:38]1[CH:39]=[CH:40][C:41]2[C:42]3[N:49]([CH2:50][CH2:51][O:52][C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[N:48][C:43]=3[CH:44]=[N:45][C:46]=2[CH:47]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 5458485-(((Tert-butoxy)carbonyl)amino)pentanoic acidHCID 670509287-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine

Produkt 1

HCID 86626156tert-butyl {4-[7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}carbamateAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, a solution of 5-(tert-butoxycarbonylamino)valeric acid (1.50 g, 6.91 mmol) in dichloroethane (30 mL) was cooled to −25° C. Triethylamine (2.40 mL, 17.2 mmol) and pivaloyl chloride (0.85 mL, 6.91 mmol) were added, and the reaction was stirred for three hours, during which time the temperature rose to −10° C. 7-Benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine (0.850 g, 2.20 mmol), prepared as described in Parts A-B of Example 46, was added in one portion followed by a small scoop of 4-dimethylaminopyridine. The reaction was allowed to warm to room temperature and stirred overnight and then heated at reflux for three hours. The reaction solution was washed with saturated sodium bicarbonate, water (2×), and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with sequentially with 98:2 and 95:5 chloroform:methanol) to yield a solid. The solid was treated with diethyl ether and concentrated under reduced pressure to provide 1.03 g of tert-butyl {4-[7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}carbamate as a white powder.

Aufarbeitung

  1. customrose to −10° C
  2. additionwas added in one portion
  3. stirringstirred overnight
  4. temperatureheated
  5. temperatureat reflux for three hours
  6. washThe reaction solution was washed with saturated sodium bicarbonate, water (2×), and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by column chromatography on silica gel (
  11. washeluting with sequentially with 98:2 and 95:5 chloroform
  12. custommethanol) to yield a solid
  13. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ac0122439eb4473bad5de374c851ebf7
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897597B2

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