Water → HCID 67371570, compound

HRID 1910901Notes

Reaction equation

HRID 1910901 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][N:11]2[CH:15]=[CH:14][CH:13]=[C:12]2[C:16]([O:18]C)=O)=[CH:5][CH:4]=1.[CH2:21]([NH2:24])[CH2:22][NH2:23].O.C(Cl)Cl>O1CCOCC1.[Cl-].[Na+].O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]23[NH:24][CH2:21][CH2:22][N:23]2[C:16](=[O:18])[C:12]2[N:11]([CH:15]=[CH:14][CH:13]=2)[CH2:10]3)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 6344DichloromethaneHCID 67367570HCID 67367570, compound

Product 1

HCID 67371570HCID 67371570, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of methyl 1-{2-[4-(hydroxymethyl)phenyl]-2-oxoethyl}-1H-pyrrole-2-carboxylate (150 mg, 0.55 mmol) in 1,4-dioxane (25 mL) was added ethane-1,2-diamine (0.75 mL, 11 mmol). The solution was heated at reflux for 54 hours. The mixture was concentrated in vacuo to give a yellow oil, which was then portioned between water (30 mL) and CH2Cl2 (30 mL). Brine was added, and the organic layer was separated. The aqueous was further extracted with CH2Cl2 (2×30 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to yield a yellow solid, which was purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient 0 to 10% methanol in EtOAc) to give 10a-[4-(hydroxymethyl)phenyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one as an off-white solid (90 mg, yield: 57%). ESI-MI m/z [M+H]+ 283.9.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 54 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customto give a yellow oil, which
  5. customthe organic layer was separated
  6. extractionThe aqueous was further extracted with CH2Cl2 (2×30 mL)
  7. dry with materialthe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield a yellow solid, which
  11. customwas purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient 0 to 10% methanol in EtOAc)

Sources & evidence

ORD record
ord-1d5cad648c8d41b6b6af88822da65bc6
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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