Triethylamine → Methyl 3-[2-({4-[(2-methoxy-6-methylpyridin-4-yl)oxy]-2-(methylamino)phenyl}amino)-2-oxoethoxy]benzoate

HRID 1843722Notes

Reaction equation

HRID 1843722 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:11]=[C:12]([NH:17][CH3:18])[C:13]([NH2:16])=[CH:14][CH:15]=2)[CH:6]=[C:5]([CH3:19])[N:4]=1.[CH3:20][O:21][C:22]([C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=1)[O:27][CH2:28][C:29](O)=[O:30])=[O:23].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:29](=[O:30])[CH2:28][O:27][C:26]3[CH:25]=[C:24]([CH:34]=[CH:33][CH:32]=3)[C:22]([O:21][CH3:20])=[O:23])=[C:12]([NH:17][CH3:18])[CH:11]=2)[CH:6]=[C:5]([CH3:19])[N:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 13816150[3-(Methoxycarbonyl)phenoxy]acetic acidHCID 667058364-[(2-Methoxy-6-methylpyridin-4-yl)oxy]-N2-methylbenzene-1,2-diamine

Product 1

HCID 66705876Methyl 3-[2-({4-[(2-methoxy-6-methylpyridin-4-yl)oxy]-2-(methylamino)phenyl}amino)-2-oxoethoxy]benzoateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction and post-treatment were carried out according to Example (16e) using 4-[(2-methoxy-6-methylpyridin-4-yl)oxy]-N2-methylbenzene-1,2-diamine produced in Example (17c) (4.13 g, 15.9 mmol), [3-(methoxycarbonyl)phenoxy]acetic acid produced in Example (1c) (3.68 g, 17.5 mmol), triethylamine (4.44 mL, 31.8 mmol), pivaloyl chloride (1.96 mL, 15.9 mmol) and dichloromethane (80 mL) to obtain the title compound (4.44 g, 64%) as a white powder.

Workup

  1. customThe reaction

Sources & evidence

ORD record
ord-62ca95a6327047729d8515484b6b5bd1
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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