Sodium Carbonate → Ethyl 5-([2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]{2-[4-(methoxy-carbonyl)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate

HRID 875320노트

반응식

HRID 875320 반응식
I[CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[O:28][C:27]([C:29]3[CH:60]=[CH:59][C:32]([CH2:33][O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[CH2:41][CH2:42][NH:43][CH:44]4[CH2:53][CH2:52][CH2:51][C:50]5[N:49]=[C:48]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH:47]=[CH:46][C:45]4=5)=[CH:31][CH:30]=3)=[N:26][C:25]=2[CH:61]=1>C(#N)C>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[O:28][C:27]([C:29]3[CH:60]=[CH:59][C:32]([CH2:33][O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[CH2:41][CH2:42][N:43]([CH2:2][CH2:3][C:4]4[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=4)[CH:44]4[CH2:53][CH2:52][CH2:51][C:50]5[N:49]=[C:48]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH:47]=[CH:46][C:45]4=5)=[CH:31][CH:30]=3)=[N:26][C:25]=2[CH:61]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 22639144Methyl 4-(2-iodoethyl)benzoate2회HCID 86709808Ethyl 5-{[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

생성물 1

HCID 86709810Ethyl 5-([2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]{2-[4-(methoxy-carbonyl)phenyl]ethyl}amino)-5,6,7,8-tetrahydroquinoline-2-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

112 mg (0.39 mmol) of methyl 4-(2-iodoethyl)benzoate and 41 mg (0.39 mmol) of anhydrous sodium carbonate were added to a solution of 149 mg (0.26 mmol) of ethyl 5-{[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate (Enantiomer 1, Example 61A) in 10 ml of dry acetonitrile, and the mixture was heated under reflux overnight. A further 112 mg of methyl 4-(2-iodoethyl)benzoate were then added, and the mixture was once more heated under reflux overnight. The reaction was then evaporated to dryness, the residue was taken up in water and ethyl acetate and the phases were separated. The organic phase was evaporated to dryness and the residue obtained was purified by preparative HPLC. This gave 72 mg (0.10 mmol, 38% of theory) of the title compound.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. temperaturethe mixture was once more heated
  4. temperatureunder reflux overnight
  5. customThe reaction was then evaporated to dryness
  6. customethyl acetate and the phases were separated
  7. customThe organic phase was evaporated to dryness
  8. customthe residue obtained
  9. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-6321b601556a48a99dd4b3cafb8ee31a
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981104B2

반응 노트

불러오는 중…