4-Amino-N-phenylbenzamide → HCID 11562741, compound

HRID 1675215Notes

Reaction equation

HRID 1675215 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][C:10](=[O:25])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[CH:19][N:20](C)C)=[C:14]([C:23]#[N:24])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2].N[C:28]1[CH:42]=[CH:41][C:31]([C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:33])=[CH:30][CH:29]=1>C(O)(=O)C.C(=O)(O)[O-].[Na+]>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][C:10](=[O:25])[NH:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:16][CH:17]=1)[N:18]=[CH:19][N:20]=[C:23]2[NH:24][C:28]1[CH:29]=[CH:30][C:31]([C:32](=[O:33])[NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:41][CH:42]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 699104-Amino-N-phenylbenzamideHCID 86617508HCID 86617508, compound

Product 1

HCID 11562741HCID 11562741, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1 g of 2-[3-cyano-4-(dimethylamino-methylene amino)-phenylcarbamoyl]-ethyl-carbamic acid t-butylester (see, Journal of Medicinal Chemistry 2004, 44:2719) dissolved in 6 ml of acetic acid was reacted with 650 mg of 4-amino-N-phenyl-benzamide at 60° C. for 3 hours, and the resulting residue was stirred in 100 ml of saturated aqueous sodium bicarbonate solution at room temperature for 30 mins. The reacted solution was extracted with 30 ml of ethylacetate 3 times, dried over anhydrous magnesium sulfate, filtered and distilled under a reduced pressure, and the resulting residue was subjected to column chromatography (eluent-chloroform:methanol=15:1) to obtain the title compound (350 mg, 25%).

Workup

  1. extractionThe reacted solution was extracted with 30 ml of ethylacetate 3 times
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-560a1b6be9eb4dfc9034c7dc495facc2
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

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