Glycine methyl ester hydrochloride → {2,5-Dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoylamino}-acetic acid methyl ester

HRID 1025895Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[C:17]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]([CH:30]4[CH2:32][CH2:31]4)[CH2:22][CH2:21]3)=[O:19])=[CH:16][N:15]=[C:14]([CH3:33])[CH:13]=2)[C:8]([Cl:34])=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH3:36][O:37][C:38](=[O:41])[CH2:39][NH2:40]>>[CH3:36][O:37][C:38](=[O:41])[CH2:39][NH:40][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([Cl:34])[C:9]([O:11][C:12]2[C:17]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]([CH:30]4[CH2:32][CH2:31]4)[CH2:22][CH2:21]3)=[O:19])=[CH:16][N:15]=[C:14]([CH3:33])[CH:13]=2)=[CH:10][C:2]=1[Cl:1]

Participants

Reactant 2

HCID 122755Glycine methyl ester hydrochloride

HCID 533114492,5-Dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoic acid

Product 1

HCID 53311535{2,5-Dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoylamino}-acetic acid methyl esterYield 39%

Procedure

The title compound was prepared in analogy to Example 29, from 2,5-dichloro-4-[5-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-2-methyl-pyridin-4-yloxy]-benzoic acid and glycine methyl ester hydrochloride (commercially available, CAS RN 5680-79-5). The compound was purified on a preparative HPLC system (Phenomenex Gemini column) with a gradient of acetonitrile:water (containing 0.05% formic acid) (50:50 to 95:5), to give 44 mg (39%) of the title compound as a light yellow solid. MS (ESI): m/z=569.136 [M+H]+.

Workup

customThe compound was purified on a preparative HPLC system (Phenomenex Gemini column) with a gradient of acetonitrile

Sources & evidence

ORD record: ord-bba76fef34244d4b87f8793896d382dd
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729091B2

Reaction notes

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