Acetic Acid → HCID 11383085, compound

HRID 2099222Notes

Reaction equation

HRID 2099222 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])[N:5]=[CH: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[C:2]4=[N:1][CH:28]=[N:30][C:20]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[C:3]4[CH:4]=[N:5]3)[CH:8]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 713FormamideHCID 114852003-(5-amino-4-benzoyl-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 11383085HCID 11383085, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

The mixture of 3-(5-Amino-4-benzoyl-pyrazol-1-yl)-N-cyclopropyl-4-methyl-benzamide (72 mg, 0.20 mmol), formamide (1.0 mL, excess), and acetic acid (0.2 mL) was heated in the microwave at 160° 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 (46 mg, 62%) as a white solid. HPLC tR=2.3 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-d16056e2118d4dd7b1d63751a218ee13
Source dataset
uspto-grants-2009_08
Patent number
US07569571B2

Reaction notes

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