O-Phenylenediamine → N-(2-Aminophenyl)-4-[1-(2-dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzamide

HRID 658044Notes

Reaction equation

HRID 658044 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][N:26]([CH3:52])[CH2:27][CH2:28][CH:29]([NH:39][C:40]([NH:42][C:43]1[CH:44]=[C:45]2[C:49](=[CH:50][CH:51]=1)[CH2:48][CH2:47][CH2:46]2)=[O:41])[C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1.[C:53]1([NH2:60])[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[NH2:59].C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[NH2:59][C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=1[NH:60][C:34](=[O:35])[C:33]1[CH:32]=[CH:31][C:30]([CH:29]([NH:39][C:40]([NH:42][C:43]2[CH:44]=[C:45]3[C:49](=[CH:50][CH:51]=2)[CH2:48][CH2:47][CH2:46]3)=[O:41])[CH2:28][CH2:27][N:26]([CH3:52])[CH3:25])=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 670498974-[1-(2-Dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzoic acid

Product 1

HCID 67421999N-(2-Aminophenyl)-4-[1-(2-dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzamideYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (250 mg, 0.66 mmol) was added to a solution of 4-[1-(2-dimethylaminoethyl)-3-(indan-5yl)ureidomethyl] benzoic acid (Reference Compound No. 10-1, 250 mg, 0.66 mmol), o-phenylenediamine (140 mg, 1.3 mmol), and N,N-diisopropylethylamine (0.33 mL, 2.0 mmol) in DMF (5.0 mL), and then the mixture was stirred at room temperature for 16 hours. Ethyl acetate (100 mL) was added thereto, and then the whole was washed with brine (50 mL) three times. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. After the residue was purified by silica gel column chromatography (chloroform-methanol), the resulting solid was collected by filtration with ethyl acetate, and then it was dried under reduced pressure to give 230 mg of the title compound as a pale yellow-white solid. (Yield 74%)

Workup

  1. washthe whole was washed with brine (50 mL) three times
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customAfter the residue was purified by silica gel column chromatography (chloroform-methanol)
  5. filtrationthe resulting solid was collected by filtration with ethyl acetate
  6. customit was dried under reduced pressure

Sources & evidence

ORD record
ord-e4bcacae6c454552a102821cf9e59839
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

Loading…