Methanone, (3-aminophenyl)phenyl- → HCID 10178531, compound

HRID 1392986Notes

Reaction equation

HRID 1392986 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.[NH2:18][C:19]1[CH:20]=[C:21]([CH:30]=[CH:31][CH:32]=1)[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23].[H-].[Na+]>CN(C)C=O>[C:22]([C:21]1[CH:20]=[C:19]([CH:32]=[CH:31][CH:30]=1)[NH:18][C:3]1[N:8]=[C:7]([C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1)(=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 17817Methanone, (3-aminophenyl)phenyl-HCID 24758Sodium hydrideHCID 20751408HCID 20751408, compound

Product 1

HCID 10178531HCID 10178531, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2-methylsulfanyl-4-(imidazo-[1,2-a]pyridin-3-yl)pyrimidine (0.146 g, 0.60 mmol) and 3-aminobenzophenone (0.238 g, 1.21 mmol) in N,N-dimethylformamide (2.5 mL) was added sodium hydride (0.061 g, 1.52 mmol) and the mixture was heated at 130° C. for 4 hours. The mixture was allowed to cool to room temperature and the solvent was removed. The residue was dissolved in water and the resulting solid was washed with water and chloroform. The organic phase was dried over MgSO4 and the solvent was evaporated. The crude product was purified by column chromatography on silica gel using chloroform/ethanol, 9:1, as the eluent affording 0.028 g (12% yield) of the title compound as a yellow solid: mp (decomp.) 237-246° C.; MS (TSP) m/z 392 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 10.25 (d, J=6.3 Hz, 1 H), 10.15 (s, 1 H), 8.74 (s, 1 H), 8.55 (d, J=5.4 Hz, 1 H), 8.29 (s, 1 H), 8.25 (d, J=8.1 Hz, 1 H), 7.87 (m, 3 H), 7.78 (t, J=7.4 Hz, 1 H), 7.67 (m, 2 H), 7.60 (m, 2 H), 7.55 (d, J=5.4 Hz, 1 H), 7.44 (d, J=7.5 Hz, 1 H), 7.20 (m, 1 H).

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was removed
  3. dissolutionThe residue was dissolved in water
  4. washthe resulting solid was washed with water and chloroform
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvent was evaporated
  7. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-70b74bc18fd54b1eb2c29c9bdfb7a8c9
Source dataset
uspto-grants-2008_03
Patent number
US07345050B2

Reaction notes

Loading…