1,2-Dichloroethane → 2-{[(4-Fluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-5-(4-morpholinylcarbonyl)benzamide

HRID 1623861Notes

Reaction equation

HRID 1623861 reaction equation
Cl.[CH3:2][C:3]1[C:7]([NH2:8])=[CH:6][O:5][N:4]=1.ON1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C(Cl)CCl.[F:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][O:40][C:41]2[CH:49]=[CH:48][C:47]([C:50]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)=[O:51])=[CH:46][C:42]=2[C:43](O)=[O:44])=[CH:35][CH:34]=1>CN(C)C=O>[F:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][O:40][C:41]2[CH:49]=[CH:48][C:47]([C:50]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)=[O:51])=[CH:46][C:42]=2[C:43]([NH:8][C:7]2[C:3]([CH3:2])=[N:4][O:5][CH:6]=2)=[O:44])=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 138042853-Methyl-1,2-oxazol-4-amine hydrochlorideHCID 671072352-{[(4-Fluorophenyl)methyl]oxy}-5-(4-morpholinylcarbonyl)benzoic acid

Product 1

HCID 681090482-{[(4-Fluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-5-(4-morpholinylcarbonyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-4-isoxazolamine hydrochloride (44.9 mg, 0.33 mmol), 1-hydroxy-7-azabenzotriazole (41.7 mg, 0.31 mmol), diisopropylethylamine (0.10 ml, 0.56 mmol) and EDC (80 mg, 0.42 mmol) were added to a solution of 2-{[(4-fluorophenyl)methyl]oxy}-5-(4-morpholinylcarbonyl)benzoic acid (100 mg, 0.28 mmol) in N,N-dimethylformamide (5 ml). The solution was stirred for 18 hours before the solvent was removed in vacuo. The residue purified by column chromatography (silica gel; 10% 7M NH3 in methanol/dichloromethane). Trituration with methanol yielded the title compound as a white solid. 21 mg.

Workup

  1. customwas removed in vacuo
  2. customThe residue purified by column chromatography (silica gel; 10% 7M NH3 in methanol/dichloromethane)

Sources & evidence

ORD record
ord-6621abea39634728aea1a97d3815bbf6
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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