2-(2,4-Dichlorobenzylidene)-3-oxobutanamide → Methyl 2-(6-carbamoyl-5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidin-2-yl)acetate

HRID 1868482Notes

Reaction equation

HRID 1868482 reaction equation
[NH2:1][C:2]1[NH:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[N:6]=1.[Cl:12][C:13]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:14]=1[CH:15]=[C:16]([C:20](=O)[CH3:21])[C:17]([NH2:19])=[O:18]>C(O)(C)C>[C:17]([C:16]1[CH:15]([C:14]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:13]=2[Cl:12])[N:3]2[CH:4]=[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[N:6]=[C:2]2[NH:1][C:20]=1[CH3:21])(=[O:18])[NH2:19]

Participants

4

Reactant 2

HCID 34229192-(2,4-Dichlorobenzylidene)-3-oxobutanamideHCID 178499562HCID 178499562, compound

Product 1

HCID 136057109Methyl 2-(6-carbamoyl-5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidin-2-yl)acetateYield 45.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of methyl 2-(2-amino-1H-imidazol-4-yl)acetate (986 mg, 6.4 mmol) and 2-(2,4-dichlorobenzylidene)-3-oxobutanamide (Example 158, Step 2, 1.64 g, 6.4 mmol) in isopropyl alcohol (40 mL) was placed as a slurry in a 100° C. oil bath. The mixture became a clear solution within 2 min and a precipitate formed during heating for 14.5 h. Upon cooling to room temperature, the tan solids were isolated by filtration with hexanes wash (2×15 mL) to provide methyl 2-(6-carbamoyl-5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidin-2-yl)acetate (1.14 g, 45%) as a tan solid.

Workup

  1. customwas placed as a slurry in a 100° C.
  2. customwithin 2 min
  3. customa precipitate formed
  4. temperatureduring heating for 14.5 h
  5. washwash (2×15 mL)

Sources & evidence

ORD record
ord-85e6e89e99994eef945d3a14684f416a
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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