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Triethylamine → Ethyl 1-cyclohexyl-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-4-oxo-1,4-dihydro-quinoline-3-carboxylate

HRID 963393
ノート
印刷プレビュー

反応式

HRID 963393 の反応式
C([C:3]1[N:4]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:5]2[C:10]([C:11](=[O:16])[C:12]=1[C:13]([OH:15])=[O:14])=[CH:9][CH:8]=[C:7](Br)[CH:6]=2)C.[C:24]([C:26]1[CH:27]=[C:28]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[CH2:29][C:30]1[C:31]([NH2:37])=[N:32][C:33]([NH2:36])=[N:34][CH:35]=1)#[CH:25].C(=O)([O-])[O-].[Na+].[Na+].[CH2:51](N(CC)CC)[CH3:52]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:18]1([N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[C:7]([C:25]#[C:24][C:26]4[CH:27]=[C:28]([CH2:29][C:30]5[C:31]([NH2:37])=[N:32][C:33]([NH2:36])=[N:34][CH:35]=5)[CH:38]=[C:39]([O:43][CH3:44])[C:40]=4[O:41][CH3:42])[CH:6]=3)[C:11](=[O:16])[C:12]([C:13]([O:15][CH2:51][CH3:52])=[O:14])=[CH:3]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 178909505-[3-Ethynyl-4,5-dimethoxy-benzyl]-pyrimidine-2,4-diamineHCID 19081638Ethyl 7-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

生成物 1

HCID 54485644Ethyl 1-cyclohexyl-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-4-oxo-1,4-dihydro-quinoline-3-carboxylate
収率 83%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
90 °C

実験手順

3 g of ethyl 7-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (Example 13ad)) are dissolved in 35 ml of N,N-dimethylformamide to 90° C. under argon with 200 mg of bis(triphenylphosphine)palladium(II) dichloride and treated dropwise within one hour with a solution of 5-[3-ethynyl-4,5-dimethoxy-benzyl]-pyrimidine-2,4-diamine (Example 11b)) in 35 ml of N,N-dimethylformamide and 35 ml of triethylamine. The dark red solution is stirred at 90° C. for a further 1 hr. The reaction mixture is left to cool to room temperature and is poured into 150 ml of 10% aqueous sodium carbonate solution while stirring. After 15 min. the suspension is suction filtered and the residue is washed with 100 ml of water and then with 100 ml of diethyl ether and dried at room temperature in a high vacuum. The crude product is triturated with 50 ml of diethyl ether for one hour, filtered off under suction and dried in a high vacuum at room temperature. 3.83 g (83%) of ethyl 1-cyclohexyl-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-4-oxo-1,4-dihydro-quinoline-3-carboxylate are obtained as a light yellow solid. M.p. 228°-230° C.

後処理

  1. waitThe reaction mixture is left
  2. temperatureto cool to room temperature
  3. stirringwhile stirring
  4. waitAfter 15 min. the suspension is
  5. filtrationsuction filtered
  6. washthe residue is washed with 100 ml of water
  7. dry with materialwith 100 ml of diethyl ether and dried at room temperature in a high vacuum
  8. customThe crude product is triturated with 50 ml of diethyl ether for one hour
  9. filtrationfiltered off under suction
  10. customdried in a high vacuum at room temperature

出典と根拠

ORDレコード
ord-7be8dc74f207445ca5b343935fbf91f8
出典データセット
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05763450

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート