Formamide → HCID 136395588, compound

HRID 2099225Notes

Reaction equation

HRID 2099225 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][C:24]([SH:27])=[CH:23][CH:22]=1.[CH:29]([NH2:31])=O>CCOC(C)=O.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:29]=[N:31][C:20]=4[C:21]3[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=3)[CH:8]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 713FormamideHCID 68529413HCID 68529413, compound

Product 1

HCID 136395588HCID 136395588, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

The mixture of 3-[5-Amino-4-(4-mercapto-benzoyl)-imidazol-1-yl]-N-cyclopropyl-4-methyl-benzamide (33 mg, 0.09 mmol), formamide (0.5 mL, excess), and p-tolunesolfonic acid (10 mg) was heated in the microwave at 180° C. for 30 min. After cooling, the mixture was diluted with EtOAc and water, and the EtOAc 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=2.47 min; MS m/z 416.27 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. customthe EtOAc 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-7a17fc032df544de916cd1038241dba0
Source dataset
uspto-grants-2009_08
Patent number
US07569571B2

Reaction notes

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