Propionic Acid → 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(methoxy-propionyl-amino)-methyl]-benzamide

HRID 2038646

Reaction equation

HRID 2038646 reaction equation
[F:1][C:2]1[C:3]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:4]([CH:12]=[C:13]([CH2:16][NH:17][O:18][CH3:19])[C:14]=1[F:15])[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6].[C:29](ON1C(=O)C2C=CC=CC=2N=N1)(=[O:32])[CH2:30][CH3:31].C(O)(=O)CC>>[F:1][C:2]1[C:3]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:4]([CH:12]=[C:13]([CH2:16][N:17]([O:18][CH3:19])[C:29](=[O:32])[CH2:30][CH3:31])[C:14]=1[F:15])[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6]

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 115335813,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-(methoxyamino-methyl)-benzamideHCID 670770954-oxo-4H-benzo[d][1,2,3]triazin-3-yl propionate

Product 1

HCID 116641403,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(methoxy-propionyl-amino)-methyl]-benzamideYield 31%

Procedure

The title compound was prepared by a procedure similar to that in Example 41. Namely, 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-(methoxyamino-methyl)-benzamide obtained in Example 15 was reacted with 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl propionate prepared from propionic acid to give 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(methoxy-propionyl-amino)-methyl]-benzamide (35.0 mg, 31%).

Workup

  1. customThe title compound was prepared by a procedure similar to that in Example 41

Sources & evidence

ORD record
ord-f0f643adf580429194761f8adb80951b
Source dataset
uspto-grants-2013_11
Patent number
US08575391B2

Linked notes

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