Water → HCID 87217684, compound

HRID 1514896Notes

Reaction equation

HRID 1514896 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[C:10]1[NH:11][C:12]2[CH:18]=[C:17]([C:19](Cl)=[O:20])[CH:16]=[CH:15][C:13]=2[N:14]=1.[NH2:22][C:23]1[CH:32]=[C:31]2[C:26]([C:27]([CH3:34])=[CH:28][C:29](=[O:33])[O:30]2)=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C.O>CCOC(C)=O>[CH3:34][C:27]1[C:26]2[C:31](=[CH:32][C:23]([NH:22][C:19]([C:17]3[CH:16]=[CH:15][C:13]4[N:14]=[C:10]([C:4]5[C:3]([CH3:2])=[CH:8][CH:7]=[CH:6][C:5]=5[CH3:9])[NH:11][C:12]=4[CH:18]=3)=[O:20])=[CH:24][CH:25]=2)[O:30][C:29](=[O:33])[CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 922497-Amino-4-methylcoumarinHCID 87217357HCID 87217357, compound

Product 1

HCID 87217684HCID 87217684, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 2-(2,6-dimethylphenyl)-3H-benzoimidazole-5-carbonyl chloride HCl salt (from Example 1-247) (160 mg) and 7-amino-4-methyl-chromen-2-one (87 mg) was added DIPEA (0.27 mL). The resulting solution was stirred at room temperature for 18 h. The mixture was partioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified by an amino column using hexanes/ethyl acetate (1:4) and gave 2-(2,6-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid (4-methyl-2-oxo-2H-chromen-7-yl)-amide as a white solid; MS (ESI)m/z 424 (M+H).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by an amino column

Sources & evidence

ORD record
ord-dbe1e44f25044225a90a6cbc9be68241
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…