2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 69695908, compound

HRID 412544Notes

Reaction equation

HRID 412544 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[NH2:17])([CH3:4])([CH3:3])[CH3:2].[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([N:39]([CH2:50][C:51](O)=[O:52])[C:40]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])=[CH:35][CH:34]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C>C(Cl)(Cl)Cl>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([N:39]([C:40]([O:42][CH2:43][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)=[O:41])[CH2:50][C:51](=[O:52])[NH:17][C:10]3[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:9]=3[NH:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:18])=[CH:35][CH:34]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 18536384HCID 18536384, compoundHCID 18536458HCID 18536458, compound

Product 1

HCID 69695908HCID 69695908, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-(2-amino-4-cyanophenyl)glycine tert-butyl ester (21.53 g) and N-[4-(1-tert-butoxycarbonylpiperidin-4-yloxy)phenyl]-N-benzyloxycarbonyl-aminoacetic acid (42.18 g) in chloroform (300 ml) was added 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (23.68 g), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:3) to give the title compound (44.479 g).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:3)

Sources & evidence

ORD record
ord-5bfa417e06fc4399952d66c20b5479ca
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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