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

HRID 598279

반응식

HRID 598279 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 86626156tert-butyl {4-[7-benzyloxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-2-yl]butyl}carbamate수율 82.6%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 3283Diethyl Ether용매HCID 63651,1-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ac0122439eb4473bad5de374c851ebf7
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897597B2

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