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

HRID 2204745Notes

Reaction equation

HRID 2204745 reaction equation
[Br:1][C:2]1[C:3]([CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(N(C(C)C)CC)(C)C.ON1C2N=CC=CC=2N=N1.Cl.[CH3:48][C:49]1[C:53]([NH2:54])=[CH:52][O:51][N:50]=1.C(Cl)CCl>CN(C)C=O>[Br:1][C:2]1[C:3]([CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])=[C:6]([CH:10]=1)[C:7]([NH:54][C:53]1[C:49]([CH3:48])=[N:50][O:51][CH:52]=1)=[O:8]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 138042853-Methyl-1,2-oxazol-4-amine hydrochlorideHCID 666113035-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid

Product 1

HCID 666106545-Bromo-2-{[(2,4-difluorophenyl)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-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid (may be prepared as described in Description 22; 150 mg, 0.34 mmol) in N,N-dimethylformamide (4 ml) was added diisopropylethylamine (0.12 ml, 0.68 mmol), 1-hydroxy-7-azabenzotriazole (55.4 mg, 0.41 mmol), 3-methyl-4-isoxazolamine hydrochloride (39.9 mg, 0.41 mmol) and EDC (98 mg, 0.51 mmol). The reaction was stirred for 18 hours. The solvent was removed in vacuo and the residue was purified by column chromatography (SiO2; ethyl acetate) to yield the title compound as a solid. 162 mg.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography (SiO2; ethyl acetate)

Sources & evidence

ORD record
ord-db44c56f6bea4df2aa6978536779d0e8
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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