Ethylenediamine → HCID 71512713、化合物

HRID 2200528ノート

反応式

HRID 2200528 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][N:11]2[C:15]([C:16]([O:18]C)=O)=[CH:14][C:13]3[CH:20]=[CH:21][S:22][C:12]2=3)=[CH:5][CH:4]=1.[CH2:24]([NH2:27])[CH2:25][NH2:26]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]23[NH:27][CH2:24][CH2:25][N:26]2[C:16](=[O:18])[C:15]2[N:11]([C:12]4[S:22][CH:21]=[CH:20][C:13]=4[CH:14]=2)[CH2:10]3)=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 3301EthylenediamineHCID 71254608HCID 71254608、化合物

生成物 1

HCID 71512713HCID 71512713、化合物収率 73.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of methyl 6-[2-(4-methoxyphenyl)-2-oxoethyl]-6H-thieno[2,3-b]pyrrole-5-carboxylate (100 mg, 0.30 mmol) in 1,4-dioxane (10 mL) was added ethylenediamine (0.78 mL, 12 mmol) and the mixture heated at reflux. The reaction was monitored by LCMS. Upon completion, the reaction mixture was concentrated in vacuo and the residue purified by flash chromatography (1 to 6% methanol-dichloromethane) to yield 11a-(4-methoxyphenyl)-2,3,11,11a-tetrahydro-1H,5H-imidazo[1,2-a]thieno[3′,2′:4,5]pyrrolo[1,2-d]pyrazin-5-one (75 mg, 73% yield) as a white solid. ESI-MI m/z [M+H]+ 340.25. 1H NMR (400 MHz, CDCl3) δ 7.31 (d, J=8.7 Hz, 2H), 7.14 (s, 1H), 6.96 (d, J=5.3 Hz, 1H), 6.82 (d, J=5.3 Hz, 1H), 6.78 (d, J=8.7 Hz, 2H), 4.52 (d, J=11.7 Hz, 1H), 4.25 (d, J=11.7 Hz, 1H), 4.02-3.89 (m, 1H), 3.73 (s, 3H), 3.64-3.51 (m, 1H), 3.37-3.26 (m, 1H), 3.08-2.94 (m, 1H).

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux
  3. concentrationUpon completion, the reaction mixture was concentrated in vacuo
  4. customthe residue purified by flash chromatography (1 to 6% methanol-dichloromethane)

出典と根拠

ORDレコード
ord-680b3e7b4bdc4708b89945dbfa232280
出典データセット
uspto-grants-2016_06
特許番号
US09359377B2

反応ノート

読み込み中…