Ethylenediamine → HCID 67368505, compound

HRID 1753117Notes

Reaction equation

HRID 1753117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][N:10]2[C:14]([C:15]([O:17]CC)=O)=[CH:13][C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[N:11]2)=[CH:4][CH:3]=1.[CH2:27]([NH2:30])[CH2:28][NH2:29]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[NH:30][CH2:27][CH2:28][N:29]2[C:15](=[O:17])[C:14]2[N:10]([N:11]=[C:12]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[CH:13]=2)[CH2:9]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 67367283HCID 67367283, compound

Product 1

HCID 67368505HCID 67368505, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 1-[2-(4-chlorophenyl)-2-oxoethyl]-3-(pyridin-2-yl)-1H-pyrazole-5-carboxylate (630 mg, 1.77 mmol) and ethane-1,2-diamine (1.77 mL, 26.6 mmol) was combined and stirred at reflux in 1,4-dioxane. After 48 hours (monitored by LCMS) the reaction mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 (20 mL) and brine (10 mL). The organic layer was separated and the aqueous layer extracted with further CH2Cl2 (2×10 mL). The combined organic layers were dried (MgSO4), filtered and evaporated in vacuo to give a yellow residue that was purified by flash column chromatography (Biotage SP4, 40 g cartridge, gradient 2 to 15% methanol in CH2Cl2). To give 10a-(4-chlorophenyl)-7-(pyridin-2-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrazolo[1,5-d]pyrazin-5-one as an off white solid (150 mg, yield: 23%). ESI-MI m/z [M+H]+ 366.1.

Workup

  1. concentrationAfter 48 hours (monitored by LCMS) the reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between CH2Cl2 (20 mL) and brine (10 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with further CH2Cl2 (2×10 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give a yellow residue that
  9. customwas purified by flash column chromatography (Biotage SP4, 40 g cartridge, gradient 2 to 15% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-e82923b7430e4dcb80ea6950cfe100d6
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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