1,2-Dichloroethane → 3-phenyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a]azepine-1-carboxylic acid

HRID 75115

反応式

HRID 75115 の反応式
CO[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]=1.[C:10]1([C:16]2[O:17][C:18](=[O:21])[CH2:19][N:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.ClCCCl.O.[OH-].[Li+]>C1COCC1.O>[C:10]1([C:16]2[N:9]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]3=[C:19]([C:18]([OH:21])=[O:17])[N:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 65073AzlactoneHCID 756572H-Azepine, 3,4,5,6-tetrahydro-7-methoxy-HCID 168937Lithium hydroxide, monohydrate

生成物 1

HCID 253421753-phenyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a]azepine-1-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

(E)-7-methoxy-3,4,5,6-tetrahydro-2H-azepine (0.395 g, 3.10 mmol) and 2-phenyloxazol-5(4H)-one (0.5 g, 3.10 mmol) were dissolved together in THF (2 mL) and DCE (2 mL) in a 5 mL microwave vial to give a orange solution. The vial was sealed and the solution was heated to 150° C. for 5 minutes. LCMS showed two peaks of the same mass (tautomers of the condensation product, Rf 0.78 and 0.83 minutes, respectively). The reaction was concentrated and the residue diluted with MeOH (1 mL) and a solution of lithium hydroxide monohydrate (0.391 g, 9.31 mmol) in water (0.5 mL). The reaction was subjected to microwave irradiation and heated at 120° C. for 5 minutes. LCMS showed a single, new peak (Rf0.53 same molecular weight) corresponding to the desired product. The reaction was concentrated to remove MeOH and then diluted with water (1 mL). The solution was acidified to pH 2 with 5M HCl and extracted with of DCM (3×2 mL). The combined organic layers were filter, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide 3-phenyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a]azepine-1-carboxylic acid (421 mg, 59%) as a brown oil that was used without further purification. LCMS (+ESI) m/z 257.1 [M+H]+.

後処理

  1. customThe vial was sealed
  2. customtautomers of the condensation product, Rf 0.78 and 0.83 minutes
  3. concentrationThe reaction was concentrated
  4. additionthe residue diluted with MeOH (1 mL)
  5. customirradiation
  6. temperatureheated at 120° C. for 5 minutes

出典と根拠

ORDレコード
ord-e079e79677014f13803bd2a95da5367b
出典データセット
uspto-grants-2014_09
特許番号
US08835422B2

関連ノート

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