2,4-Dichlorobenzylamine → HCID 25029940, compound

HRID 546272Notes

Reaction equation

HRID 546272 reaction equation
[CH2:1]([N:3]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]1[C:13]([OH:15])=O)[CH3:2].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[Cl:35][C:36]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:37]=1[CH2:43][NH2:44].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.O>[Cl:35][C:36]1[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:37]=1[CH2:43][NH:44][C:13]([CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11](=[O:12])[N:3]1[CH2:1][CH3:2])=[O:15]

Participants

8

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67201188HCID 67201188, compound

Product 1

HCID 25029940HCID 25029940, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Ethyl-3-oxo-2,3-dihydro-1H-isoindole-1-carboxylic acid (0.061 g, 0.3 mmol, prepared as described below) was dissolved in anhydrous dimethylformamide (5 ml) and to this was added 1-hydroxybenzotriazole (0.045 g, 0.3 mmol), diisopropylethylamine (0.105 ml, 0.6 mmol), [(2,4-dichlorophenyl)methyl]amine (0.054 g, 0.3 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.114 g, 0.3 mmol). The mixture was stirred for 3 hrs and then left to stand overnight. The mixture was diluted with water (50 ml) and a little saturated aqueous sodium chloride solution and extracted with ethyl acetate (3×20 ml). The organic fractions were combined and washed with 10% aqueous sodium carbonate (50 ml) and then with saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulphate and evaporated to give a gum. The gum was purified by mass-directed automated HPLC to give N-[(2,4-dichlorophenyl)methyl]-2-ethyl-3-oxo-2,3-dihydro-1H-isoindole-1-carboxamide (0.056 g).

Workup

  1. waitleft
  2. waitto stand overnight
  3. extractiona little saturated aqueous sodium chloride solution and extracted with ethyl acetate (3×20 ml)
  4. washwashed with 10% aqueous sodium carbonate (50 ml)
  5. dry with materialwith saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulphate
  6. customevaporated
  7. customto give a gum
  8. customThe gum was purified

Sources & evidence

ORD record
ord-a6856e1055864805b582780882ab331e
Source dataset
uspto-grants-2011_05
Patent number
US07935832B2

Reaction notes

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