Ethyl Acrylate → Ethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoate

HRID 2059939ノート

反応式

HRID 2059939 の反応式
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:25]([CH3:34])=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH2:30][NH:29][CH2:28][CH2:27]4)[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17].N12CCCN=C1CCCCC2.[C:46]([O:50][CH2:51][CH3:52])(=[O:49])[CH:47]=[CH2:48]>C(#N)C>[Cl:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[C:25]([CH3:34])=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH2:30][N:29]([CH2:48][CH2:47][C:46]([O:50][CH2:51][CH3:52])=[O:49])[CH2:28][CH2:27]4)[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]

参加物

5

反応物 3

HCID 8821Ethyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 684983726-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-1,2,3,4-tetrahydroisoquinoline trifluoroacetate

生成物 1

HCID 59370484Ethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoate収率 103.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

To a suspension of 6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-1,2,3,4-tetrahydroisoquinoline trifluoroacetate (Example 10; 90 mg; 0.18 mmol) in acetonitrile (3 ml) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 0.16 ml; 1.09 mmol). Ethyl acrylate (0.03 ml; 0.27 mmol) was added to the solution and the resulting mixture stirred at 70° C. for 0.5 h. The mixture was cooled to room temperature and the solvent removed. The residue was partitioned between ethyl acetate and brine, and the aqueous layer further extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (90 mg).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent removed
  3. customThe residue was partitioned between ethyl acetate and brine
  4. extractionthe aqueous layer further extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f96b86cdc35c4c3ea25168d6795eb8ac
出典データセット
uspto-grants-2012_10
特許番号
US08278324B2

反応ノート

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