HCID 2794657, compound → 4-{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester

HRID 1025866Notes

Reaction equation

HRID 1025866 reaction equation
COC(=O)[CH2:4][NH:5][C:6](=[O:37])[C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:21]([N:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH:33]3[CH2:35][CH2:34]3)[CH2:25][CH2:24]2)=[O:22])=[CH:9][C:8]=1[Cl:36].[CH3:39][O:40][C:41]([C:43]1[N:44]([CH3:49])[CH:45]=C(N)[CH:47]=1)=[O:42]>CCCCCCC.C(OCC)(=O)C>[CH3:39][O:40][C:41]([C:43]1[N:44]([CH3:49])[CH:45]=[C:4]([NH:5][C:6](=[O:37])[C:7]2[CH:12]=[C:11]([Cl:13])[C:10]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][C:16]=3[C:21]([N:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH:33]4[CH2:35][CH2:34]4)[CH2:25][CH2:24]3)=[O:22])=[CH:9][C:8]=2[Cl:36])[CH:47]=1)=[O:42]

Participants

4

Reactant 2

HCID 2794657HCID 2794657, compoundHCID 53312194{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-acetic acid methyl ester

Product 1

HCID 533123634-{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to Example 1, from 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid (Example 29, intermediate) and 4-amino-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (commercially available, CAS RN 180258-45-1) and using a gradient of n-heptane:ethyl acetate (100:0 to 0:100) for the chromatiographic purification. Light brown foam (70%). MS (ESI): m/z=620.147 [M+H]+.

Workup

  1. customfor the chromatiographic purification

Sources & evidence

ORD record
ord-856ec836620041b79f2897c2ef81a6d2
Source dataset
uspto-grants-2014_05
Patent number
US08729091B2

Reaction notes

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