1,5-Diazabicyclo(4.3.0)non-5-ene → HCID 178420741, compound

HRID 1348546Notes

Reaction equation

HRID 1348546 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([C:15]([O:17]CC)=O)[C:10]([O:12]CC)=O.Cl.[NH2:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.[CH2:27]1[CH2:35][N:34]2[C:29](=[N:30][CH2:31][CH2:32][CH2:33]2)[CH2:28]1>CN(C)C=O>[OH:17][C:15]1[N:23]2[CH:24]=[CH:25][N:26]=[C:22]2[N:21]=[C:10]([OH:12])[C:9]=1[C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1].[CH2:27]1[CH2:35][N:34]2[C:29](=[N:30][CH2:31][CH2:32][CH2:33]2)[CH2:28]1

Participants

5

Reactant 3

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 2782658Diethyl 2-(2-chloro-6-fluorophenyl)malonateHCID 122112381H-Imidazol-2-amine hydrochloride

Product 1

HCID 178420741HCID 178420741, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.89 g of diethyl (2-chloro-6-fluorophenyl)malonate, 1.20 g of aminoimidazole hydrochloride, 2.48 g of 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) and 10 ml of N,N-dimethylformamide (DMF) was heated at 100° C. for 4 hours. The reaction mixture was allowed to cool, filtered the precipitate and dried to give 1.80 g of 5,7-dihydroxy-6-(2-chloro-6-fluorophenyl)imidazo[1,2-a]pyrimidine DBN salt.

Workup

  1. temperatureto cool
  2. filtrationfiltered the precipitate
  3. customdried

Sources & evidence

ORD record
ord-f483e3bf53794d85b2583432dbceba08
Source dataset
uspto-grants-2007_05
Patent number
US07211545B2

Reaction notes

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