Acetic Acid → N-Cyclopropyl-4-methyl-3-(6-phenyl-purin-9-yl)-benzamide

HRID 2099223Notes

Reaction equation

HRID 2099223 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[CH:5]=[N:4][C:3]=1[C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH:28]([NH2:30])=O.C(O)(=O)C>C(Cl)Cl.O>[CH:13]1([NH:12][C:10](=[O:11])[C:9]2[CH:16]=[CH:17][C:18]([CH3:19])=[C:7]([N:6]3[CH:5]=[N:4][C:3]4[C:2]3=[N:1][CH:28]=[N:30][C:20]=4[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:8]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 713FormamideHCID 248606083-(5-Amino-4-benzoyl-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide

Product 1

HCID 11632078N-Cyclopropyl-4-methyl-3-(6-phenyl-purin-9-yl)-benzamideYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

The mixture of 3-(5-amino-4-benzoyl-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide (33 mg, 0.09 mmol), formamide (0.5 mL, excess), and acetic acid (0.1 mL) was heated in the microwave at 200° C. for 20 min. After cooling, the mixture was diluted with CH2Cl2 and water, and the CH2Cl2 layer was separated, dried over Na2SO4, filtered and concentrated. The crude product was purified by preparatory HPLC to provide the title compound (20 mg, 59%) as a white solid: HPLC tR=2.20 min; MS m/z 370.3 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. customthe CH2Cl2 layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparatory HPLC

Sources & evidence

ORD record
ord-24fa66d406ff4c41997d2b536ed20fd0
Source dataset
uspto-grants-2009_08
Patent number
US07569571B2

Reaction notes

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