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

HRID 2204740Notes

Reaction equation

HRID 2204740 reaction equation
[Br:1][C:2]1[C:3]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH3:27][C:28]1[C:32]([NH2:33])=[CH:31][O:30][N:29]=1.C(N(C(C)C)CC)(C)C.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C)C=O>[Br:1][C:2]1[C:3]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)=[C:6]([CH:10]=1)[C:7]([NH:33][C:32]1[C:28]([CH3:27])=[N:29][O:30][CH:31]=1)=[O:9]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 138042843-Methyl-1,2-oxazol-4-amineHCID 666117265-Bromo-2-{[(4-fluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid

Product 1

HCID 666118605-Bromo-2-{[(4-fluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-4-(4-morpholinylmethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid (may be prepared as described in Description 20; 150 mg, 0.35 mmol) in N,N-dimethylformamide (4 ml) was added 3-methyl-4-isoxazolamine (41.6 mg, 0.42 mmol), diisopropylethylamine (0.12 ml, 0.71 mmol), 1-hydroxy-7-azabenzotriazole (57.7 mg, 0.42 mmol) and EDC (102 mg, 0.53 mmol). The mixture was stirred for 18 hours, then the solvent removed in vacuo to give a residue. The residue was purified by column chromatography (10% 7M NH3 in methanol/dichloromethane) to yield the title compound as a solid. 178 mg.

Workup

  1. customthe solvent removed in vacuo
  2. customto give a residue
  3. customThe residue was purified by column chromatography (10% 7M NH3 in methanol/dichloromethane)

Sources & evidence

ORD record
ord-a0a7fdc40f1c4e5795d0aaff986a3272
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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