Diphosgene → HCID 25262942, compound

HRID 2059715Notes

Reaction equation

HRID 2059715 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[NH:10][C:11]1[N:15]2[CH:16]=[CH:17][CH:18]=[N:19][C:14]2=[N:13][C:12]=1[C:20]1[C:29]([O:30][CH3:31])=[CH:28][C:27]([O:32][CH3:33])=[CH:26][C:21]=1[C:22]([NH:24][NH2:25])=[O:23].Cl[C:35](OC(Cl)(Cl)Cl)=[O:36]>O1CCOCC1>[Cl:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[C:4]=1[NH:10][C:11]1[N:15]2[CH:16]=[CH:17][CH:18]=[N:19][C:14]2=[N:13][C:12]=1[C:20]1[C:29]([O:30][CH3:31])=[CH:28][C:27]([O:32][CH3:33])=[CH:26][C:21]=1[C:22]1[O:23][C:35](=[O:36])[NH:25][N:24]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 67543381HCID 67543381, compound

Product 1

HCID 25262942HCID 25262942, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

115 mg of 2-[3-(2,6-dichlorophenylamino)imidazo[1,2-a]pyrimidin-2-yl]-3,5-dimethoxybenzohydrazide hydrochloride and 26 μl of trichloromethyl chloroformate (diphosgene) are heated under reflux for 2 hours in 5 ml of dioxane. The reaction mixture is evaporated, and water and DCM are added. The aqueous phase is rendered neutral, extracted a number of times with DCM, and the combined organic phases are dried and evaporated. Purification by column chromatography (ethyl acetate/methanol) and washing of the resultant solid by stirring with heptane gives 35 mg (33%) of “A6”; MS-FAB (M+H+)=499.4; Rf (polar method): 1.61 min.

Workup

  1. customThe reaction mixture is evaporated
  2. additionwater and DCM are added
  3. extractionextracted a number of times with DCM
  4. customthe combined organic phases are dried
  5. customevaporated
  6. customPurification by column chromatography (ethyl acetate/methanol)
  7. washwashing of the resultant solid

Sources & evidence

ORD record
ord-e02296d405e24fc69606fc22f1e0fb18
Source dataset
uspto-grants-2012_10
Patent number
US08278312B2

Reaction notes

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