Dimethyl 4-aminoheptanedioate → 4-{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-heptanedioic acid dimethyl ester

HRID 1967033Notes

Reaction equation

HRID 1967033 reaction equation
COC(=O)C[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](=[O:52])[CH2:42][CH2:43][CH:44](N)[CH2:45][CH2:46][C:47]([O:49][CH3:50])=[O:48]>CCCCCCC.C(OCC)(=O)C>[CH3:50][O:49][C:47](=[O:48])[CH2:46][CH2:45][CH:44]([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[CH2:34][CH2:35]3)[CH2:25][CH2:24]2)=[O:22])=[CH:9][C:8]=1[Cl:36])[CH2:43][CH2:42][C:41]([O:40][CH3:39])=[O:52]

Participants

4

Reactant 2

HCID 14537432Dimethyl 4-aminoheptanedioateHCID 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 533112724-{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-heptanedioic acid dimethyl 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-heptanedioic acid dimethyl ester (J. Am. Chem. Soc. 2005, 127 (50), 17877-17887) and using a gradient of n-heptane:ethyl acetate (100:0 to 0:100) for the chromatographic purification. Light brown foam (69%). MS (ESI): m/z=669.19 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-f93e9fcf816e442298ab878098de34c4
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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