Ethylenediamine → HCID 71512713, 화합물

HRID 2200528노트

반응식

HRID 2200528 반응식
[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

참가 물질

4

반응물 2

HCID 3301EthylenediamineHCID 71254608HCID 71254608, 화합물

생성물 1

HCID 71512713HCID 71512713, 화합물수율 73.7%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-680b3e7b4bdc4708b89945dbfa232280
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359377B2

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