m-Toluidine → HCID 178425550, compound

HRID 227624Notes

Reaction equation

HRID 227624 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[N:26][C:27]#[N:28])OC4C=CC=CC=4)=[CH:13][CH:12]=3)=[C:9]([CH3:29])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34]>CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:34][C:33]4[CH:35]=[CH:36][CH:37]=[C:31]([CH3:30])[CH:32]=4)=[N:26][C:27]#[N:28])=[CH:13][CH:12]=3)=[C:9]([CH3:29])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 178435033HCID 178435033, compound

Product 1

HCID 178425550HCID 178425550, compoundYield 362.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 132 (40 mg, 0.01 mmol) and 3-methylaniline (0.012 mL, 0.01 mmol) in DMF (1 mL) was heated in a Smith synthesizer microwave to 180° C. for 22 minutes and partitioned between water and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate and the combined extracts were washed with water and brine, dried (Na2SO4), filtered and concentrated. The concentrate was purified by flash column chromatography on silica gel with 8% methanol/dichloromethane to provide the desired product (15 mg). MS(ESI(+)) m/e 414 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 9.65 (s, 1H); 9.48 (s, 1H); 8.26 (s, 1H); 7.45 (d, J=8.4 Hz, 2H); 7.35 (d, J=8.4 Hz, 2H); 7.23 (t, J=7.8 Hz, 1H); 7.15-7.10 (m, 2H); 6.96 (d, J=7.8 Hz, 1H); 2.29 (s, 6H).

Workup

  1. custompartitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. washthe combined extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 8% methanol/dichloromethane

Sources & evidence

ORD record
ord-490c9814c84a440290340c4c37d199eb
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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