Triethylamine → methyl N-(2,6-dichlorobenzoyl)-3-[2-(2,6-dichlorophenyl)-6-quinolyl]alaninate

HRID 1869782Notes

Reaction equation

HRID 1869782 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].C(N(CC)CC)C.[Cl:33][C:34]1[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:35]=1[C:36](Cl)=[O:37]>C(Cl)Cl>[Cl:33][C:34]1[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:35]=1[C:36]([NH: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])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 24755559Methyl 3-[2-(2,6-dichlorophenyl)quinolin-6-yl]alaninate

Product 1

HCID 10482608methyl N-(2,6-dichlorobenzoyl)-3-[2-(2,6-dichlorophenyl)-6-quinolyl]alaninate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 23.38 g of methyl 2-amino-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 33 (0.2 TFA salt) in CH2Cl2 (50 ml) are added, at 0° C., triethylamine (22 ml) and 2,6-dichlorobenzoyl chloride (6.22 ml) dissolved in CH2Cl2 (6 ml). The reaction is stirred at RT for 2 h. The organic phase is washed with water, dried over MgSO4 and evaporated under vacuum. The residue is purified by silica gel chromatography using CH2Cl2/Hexane 95/5 as eluent.

Workup

  1. washThe organic phase is washed with water
  2. dry with materialdried over MgSO4
  3. customevaporated under vacuum
  4. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-8c6a343e0555438abd0a3c549b80650a
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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