Potassium hydroxy sulfite → 3-{4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid methyl ester

HRID 1515012Notes

Reaction equation

HRID 1515012 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[NH2:21])[C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:6].[CH3:22][O:23][C:24](=[O:37])[CH2:25][CH2:26][C:27]1[CH:32]=[C:31](C)[C:30]([CH:34]=O)=[C:29](C)[CH:28]=1.OOS([O-])=O.[K+]>CN(C=O)C.O>[CH3:22][O:23][C:24](=[O:37])[CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:34]2[NH:1][C:2]3[CH:3]=[C:4]([C:5](=[O:6])[NH:7][C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)[CH:18]=[CH:19][C:20]=3[N:21]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 23707502Potassium hydroxy sulfiteHCID 54209618Methyl 3-(3,5-dimethyl-4-formylphenyl)propionateHCID 669657403,4-diamino-N-quinolin-2-yl-benzamide

Product 1

HCID 669657603-{4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3,4-diamino-N-quinolin-2-yl-benzamide (1.0 g, 3.92 mmol) and 3-(4-formyl-3,5-dimethyl-phenyl)-propionic acid methyl ester (1.09 g, 3.92 mmol) in DMF (10 mL) and water (1 mL) was added oxone (1.62 g, 2.63 mmol) and the mixture was stirred atambient temperature for 20 min. The mixture was quenched with water and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (1:3) to give 3-{4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid methyl ester as a pale yellow solid. 1H NMR (Methanol-d4, 400 MHz): δ 8.45 (d, 1H), 8.38 (d, 1H), 8.29 (s, 1H), 8.04 (d, 1H), 7.93 (d, 2H), 7.83 (s, 1H), 7.75 (m, 1H), 7.55 (m, 1H), 7.09 (s, 2H), 3.67 (s, 3H), 2.97 (t, 2H), 2.71 (t, 2H), 2.16 (s, 6H). MS (m/z) 479.2 (M+1); Retention time: 1.48 min (Method 10).

Workup

  1. customThe mixture was quenched with water
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-419af10fa0254d98966be4e3d05a15ac
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…