Chloroform → N-ethyl-4-methyl-3-(1-methylphthalazin-6-yl)benzamide

HRID 422551Notes

Reaction equation

HRID 422551 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([CH3:21])=[N:16][N:15]=[CH:14]2.[CH2:22]([NH2:24])[CH3:23].C1COCC1.C(Cl)(Cl)Cl>CCOC(C)=O.CN(C)C=O>[CH2:22]([NH:24][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([CH3:21])=[N:16][N:15]=[CH:14]3)[CH:4]=1)[CH3:23]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6341EthylamineHCID 8028TetrahydrofuranHCID 597260224-Methyl-3-(1-methylphthalazin-6-yl)benzoic acid

Product 1

HCID 59726016N-ethyl-4-methyl-3-(1-methylphthalazin-6-yl)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a 15-ml round-bottom flask were added 4-methyl-3-(1-methylphthalazin-6-yl)benzoic acid (51 mg, 183 μmol), hatu (105 mg, 275 μmol), ethylamine (2M solution in THF (275 μl, 550 μmol), and chloroform (1000 μl). 0.5 ml of N,N-Dimethylformamide was next added to the mixture, and the resulting golden yellow solution was stirred at RT for 3 h, during which LC-MS indicated completion of reaction. The reaction mixture was diluted with EtOAc and washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo. CombiFlash purification (1% to 5% MeOH/CH2Cl2) afforded the title compound (26) as a tan amorphous solid. MS (ES+): 306.2 (M+H)+.

Workup

  1. customcompletion of reaction
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customCombiFlash purification (1% to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e67aa7034d8f46d5a5ff3faf92c138df
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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