Cesium carbonate → HCID 178492026, compound

HRID 2174948Notes

Reaction equation

HRID 2174948 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([NH2:12])=[C:5]2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[O:22][CH3:23].C[S-](C)[C:26]([S-])=[N:27][C:28]#[N:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:26](=[N:27][C:28]#[N:29])[N:13]([C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=4[O:22][CH3:23])[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 66664633HCID 66664633, compoundHCID 178503843HCID 178503843, compound

Product 1

HCID 178492026HCID 178492026, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To the stirred solution of 6-bromo-N4-(2,4-dimethoxyphenyl)quinoline-3,4-diamine (10.69 mmol) in DMF (10 mL) was added dimethylcyanocarbonimidodithioate (16.03 mmol) followed by cesium carbonate (32.1 mmol) and the resulting reaction mixture was heated at 80° C. for 18 h. Completion of reaction was monitored by TLC, solvent evaporated under reduced pressure. Residue was diluted with water & extracted with ethyl acetate (250 mlx 5), organic layer were dried over anhydrous Na2SO4 and evaporated under vacuum. Crude product was further purified on silica gel column using MeOH/CHCl3 (8%) as elute to afford desired product as off-white solid. 1H NMR (300 MHz, DMSO-d6): δ 13.72 (s, 1H), 8.93 (s, 1H), 8.03 (d, J=9 Hz, 1H), 7.77 (dd, J=3.9 Hz, 1H), 7.58 (d, J=9 Hz, 1H), 7.16 (d, J=3 Hz, 1H), 6.93 (d, J=3 Hz, 1H), 6.84 (dd, J=3, 9 Hz, 1H), 3.92 (s, 3H), 3.69 (s, 3H); MS (m/z): 424 (M+1)+.

Workup

  1. customthe resulting reaction mixture
  2. customCompletion of reaction
  3. customevaporated under reduced pressure
  4. additionResidue was diluted with water
  5. extractionextracted with ethyl acetate (250 mlx 5), organic layer
  6. dry with materialwere dried over anhydrous Na2SO4
  7. customevaporated under vacuum
  8. customCrude product was further purified on silica gel column
  9. washas elute

Sources & evidence

ORD record
ord-d952cebe729e412cbfce43f36fd419d7
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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