Ethylenediamine → HCID 71512713, compound

HRID 2200528Notes

Reaction equation

HRID 2200528 reaction equation
[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

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 71254608HCID 71254608, compound

Product 1

HCID 71512713HCID 71512713, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-680b3e7b4bdc4708b89945dbfa232280
Source dataset
uspto-grants-2016_06
Patent number
US09359377B2

Reaction notes

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