Triethylamine → N-(3-dimethylaminophenyl)-4-methyl-3-(5-methylisoxazol-3-ylcarbonylamino)benzamide

HRID 502028Notes

Reaction equation

HRID 502028 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]([CH3:23])[CH3:22])[CH:16]=1)=[O:13].[CH3:28][C:29]1[O:33][N:32]=[C:31]([C:34](Cl)=[O:35])[CH:30]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:22][N:21]([CH3:23])[C:17]1[CH:16]=[C:15]([NH:14][C:12](=[O:13])[C:11]2[CH:24]=[CH:25][C:26]([CH3:27])=[C:9]([NH:8][C:34]([C:31]3[CH:30]=[C:29]([CH3:28])[O:33][N:32]=3)=[O:35])[CH:10]=2)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27368945-Methylisoxazole-3-carbonyl chlorideHCID 226361113-amino-N-(3-dimethylaminophenyl)-4-methylbenzamide

Product 1

HCID 22636165N-(3-dimethylaminophenyl)-4-methyl-3-(5-methylisoxazol-3-ylcarbonylamino)benzamideYield 71.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.129 ml) was added to a stirred mixture of 3-amino-N-(3-dimethylaminophenyl)-4-methylbenzamide (0.1 g), 4-dimethylaminopyridine (5 mg), 5-methylisoxazol-3-ylcarbonyl chloride (0.081 g) and methylene chloride (3 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The mixture was diluted with methylene chloride (10 ml), washed with a saturated aqueous sodium bicarbonate solution and dried over magnesium sulphate. The organic solution was evaporated and the residue was triturated under isohexane. The resultant solid was dried at 55° C. under vacuum to give the title compound as a solid (0.1 g); NMR Spectrum: (CDCl3) 2.42 (s, 3H), 2.55 (s, 3H), 2.97 (s, 6H), 6.55 (m, 2H), 6.89 (d, 1H), 7.23 (m, 2H), 7.36 (d, 1H), 7.72 (d, 1H), 7.84 (broad s, 1H), 8.55 (broad s, 2H); Mass Spectrum: M+H+ 379.

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. customThe organic solution was evaporated
  4. customthe residue was triturated under isohexane
  5. customThe resultant solid was dried at 55° C. under vacuum

Sources & evidence

ORD record
ord-6ddecbe729484b51be47132e7af049de
Source dataset
uspto-grants-2010_08
Patent number
US07772432B2

Reaction notes

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