Water → HCID 178501558, compound

HRID 1514981Notes

Reaction equation

HRID 1514981 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]=O)=[C:8]([CH3:15])[CH:7]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:32]=[CH:33][C:34]=1[NH2:35])[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH3:31])[CH:25]=1)=[O:22].C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].O>CS(C)=O.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2].CCOC(C)=O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:35][C:34]3[CH:33]=[CH:32][C:20]([C:21](=[O:22])[NH:23][C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH3:31])[CH:25]=4)=[CH:19][C:18]=3[N:17]=2)=[C:8]([CH3:15])[CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 2733225Ytterbium triflateHCID 66965643HCID 66965643, compoundHCID 86638178HCID 86638178, compound

Product 1

HCID 178501558HCID 178501558, compound

Reagents, catalysts & solvents 3

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-formyl-3,5-dimethylphenylamino)-acetic acid methyl ester (800 mg) and 3,4-diamino-N-(3,4-dimethylphenyl)-benzamide (694 mg) in DMSO (15 mL) was added Yb(OTf)3 (390 mg) and Cu(OTf)2 (228 mg). The solution was stirred at room temperature for 18 h then the reaction mixture was partioned between water and EtOAc The aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified by flash chromatography (amino-column) using hexanes/ethyl acetate (1:4) to give {4-[5-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenylamino}-acetic acid methyl ester as a light yellow solid. MS (ESI)m/z 457 (M+H); 1H NMR (MeOD, 400 MHz) δ 8.21 (s, 1H), 7.85 (dd, 1H), 7.67 (s, 1H), 7.47 (d, 1H), 7.42 (dd, 1H), 7.12 (d, 1H), 6.42 (s, 2H), 3.97 (s, 2H), 3.75 (s, 3H), 2.29 (s, 3H), 2.26 (s, 3H), 2.09 (s, 6H).

Workup

  1. extractionwas extracted with EtOAc
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (amino-column)

Sources & evidence

ORD record
ord-f307d2b7efb74ee08e8b8cd761065df8
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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