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 875320ノート

反応式

HRID 875320 の反応式
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

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 22639144Methyl 4-(2-iodoethyl)benzoate2 回HCID 86709808Ethyl 5-{[2-(2-{[4-(5-chloro-1,3-benzoxazol-2-yl)benzyl]oxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylate

生成物 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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6321b601556a48a99dd4b3cafb8ee31a
出典データセット
uspto-grants-2015_03
特許番号
US08981104B2

反応ノート

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