Diisopropylethylamine → Methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-[(2-isopropoxy-3,4-dioxo-1-cyclobuten-1-yl)amino]propanoate

HRID 1869808Notes

Reaction equation

HRID 1869808 reaction equation
[NH2:1][CH:2]([CH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])[CH:12]=[CH:11]2)[C:3]([O:5][CH3:6])=[O:4].CCN(C(C)C)C(C)C.[CH:35]([O:38][C:39]1[C:40](=O)[C:41](=[O:47])[C:42]=1[O:43]C(C)C)([CH3:37])[CH3:36]>CO>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([Cl:24])[C:18]=1[C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:16][CH:17]=[C:8]([CH2:7][CH:2]([NH:1][C:40]3[C:41](=[O:47])[C:42](=[O:43])[C:39]=3[O:38][CH:35]([CH3:37])[CH3:36])[C:3]([O:5][CH3:6])=[O:4])[CH:9]=2)[N:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1823143,4-Diisopropoxy-3-cyclobutene-1,2-dioneHCID 24755559Methyl 3-[2-(2,6-dichlorophenyl)quinolin-6-yl]alaninate

Product 1

HCID 57987604Methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-[(2-isopropoxy-3,4-dioxo-1-cyclobuten-1-yl)amino]propanoateYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-amino-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 33 (2 TFA salt, 1.51 g) in CH3OH (15 ml) cooled with an ice bath, are added 0.96 ml of DIPEA and 495.6 mg of 3,4-diisopropoxy-3-cyclobutene-1,2-dione. The solution is stirred overnight at Rt. The solution is evaporated and the resulting residue is purified over silica gel using CH2Cl2/CH3OH (99.2/0.8) as eluent to give methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-[(2-isopropoxy-3,4-dioxo-1-cyclobuten-1-yl)amino]propanoate 116.

Workup

  1. customThe solution is evaporated
  2. customthe resulting residue is purified over silica gel

Sources & evidence

ORD record
ord-b11a5cb2a29b4cdbab29b731dd12937c
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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