Ethylenediamine → HCID 67370128, compound

HRID 1753170Notes

Reaction equation

HRID 1753170 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[C:15]([O:17]C)=O)=[CH:4][CH:3]=1.[CH2:20]([NH2:23])[CH2:21][NH2:22]>O1CCOCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[NH:23][CH2:20][CH2:21][N:22]2[C:15](=[O:17])[C:11]2[N:10]([CH:14]=[CH:13][CH:12]=2)[CH2:9]3)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3301Ethylenediamine2×HCID 23248984HCID 23248984, compound

Product 1

HCID 67370128HCID 67370128, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 1-[2-(4-hydroxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate (200 mg, 0.77 mmol) in 1,4-dioxane (40 mL) was added ethane-1,2-diamine (1 mL, 15 mmol), after 48 h extra ethane-1,2-diamine (1 mL, 15 mmol) was added and the mixture heated for 48 additional hours. After that time 90% of the starting material was converted into the above product. The resulting mixture was then concentrated in vacuo to give a residue that was purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient 0-10% MeOH in CH2Cl2) to give 10a-(4-hydroxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (180 mg, yield: 86%). ESI-MI m/z [M+H]+ 270.1.

Workup

  1. temperaturethe mixture heated for 48 additional hours
  2. concentrationThe resulting mixture was then concentrated in vacuo
  3. customto give a residue that
  4. customwas purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient 0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-7bd2dfda9a9648ddb099b10dd442f142
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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