Dimethylbarbituric acid → Ethoxy-[4-(2-hydroxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-acetic acid ethyl ester

HRID 63949ノート

反応式

HRID 63949 の反応式
[CH2:1]([O:3][C:4](=[O:34])[CH:5]([C:9]1[C:10]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[O:30]CC=C)=[C:11]2[C:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C:17]=3[S:16][C:12]2=[N:13][C:14]=1[CH3:15])[O:6][CH2:7][CH3:8])[CH3:2].CN1C(=O)CC(=O)N(C)C1=O>ClCCl>[CH2:1]([O:3][C:4](=[O:34])[CH:5]([O:6][CH2:7][CH3:8])[C:9]1[C:10]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[OH:30])=[C:11]2[C:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C:17]=3[S:16][C:12]2=[N:13][C:14]=1[CH3:15])[CH3:2]

参加物

4

反応物 2

HCID 69860Dimethylbarbituric acidHCID 69672825[4-(2-Allyloxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-ethoxy-acetic acid ethyl ester

生成物 1

HCID 136372354Ethoxy-[4-(2-hydroxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-acetic acid ethyl ester収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of [4-(2-Allyloxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-ethoxy-acetic acid ethyl ester (22 mg, 46 μmols) in dichloromethane (3 mL) was added 1,3-dimethylbarbituric acid (38 mg, 240 μmols, 5 eq), and the reaction was evacuated and filled with nitrogen. Palladium tetrakis(triphenylphosphine) (1.2 mg, 2 mol %) was added and the reaction was heated to reflux for 16 hours. The reaction was concentrated in vacuo. The residue was purified using ISCO Companion with a Redisep silica gel 4 g cartridge and a gradient of heptane and ethyl acetate (0% to 40%). Fractions containing desired product were combined and concentrated in vacuo to give ethoxy-[4-(2-hydroxy-4-methyl-phenyl)-2-methyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl]-acetic acid ethyl ester as a pale yellow oil, 20 mg (95% yield). LC-MS (12 min acidic) 6.40 mins 58-69% pure by UV, ES+/APCI+ 440, ES−/APCI− 438; 6.66 mins 27-31% pure by UV, ES+/APCI+ 440, ES−/APCI− 438.

後処理

  1. customthe reaction was evacuated
  2. additionfilled with nitrogen
  3. additionPalladium tetrakis(triphenylphosphine) (1.2 mg, 2 mol %) was added
  4. temperaturethe reaction was heated
  5. temperatureto reflux for 16 hours
  6. concentrationThe reaction was concentrated in vacuo
  7. customThe residue was purified
  8. additionFractions containing desired product
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a230e82915c44e89bb04deabaa0d1a73
出典データセット
uspto-grants-2016_09
特許番号
US09447116B2

反応ノート

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