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

HRID 2204743Notes

Reaction equation

HRID 2204743 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]([OH:9])=O.[NH2:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=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]([CH2:21][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:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:9]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 666113035-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid

Product 1

HCID 666119545-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamide

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 3-aminopyridine (38.3 mg, 0.41 mmol), diisopropylethylamine (0.12 ml, 0.68 mmol), 1-hydroxy-7-azabenzotriazole (55.4 mg, 0.41 mmol) and EDC (98 mg, 0.51 mmol). The mixture was stirred overnight and the solvent removed in vacuo to give a residue. Purification by column chromatography (SiO2; 10% 7M NH3 in methanol/dichloromethane) yielded the title compound as a solid. 162 mg.

Workup

  1. customthe solvent removed in vacuo
  2. customto give a residue
  3. customPurification by column chromatography (SiO2; 10% 7M NH3 in methanol/dichloromethane)

Sources & evidence

ORD record
ord-3239d45288eb480888f1128b84d9cf8d
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

Loading…