1,3-Dichloro-2-isocyanatobenzene → Methyl 2-{[(2,6-dichloroanilino)carbonyl]amino}-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate

HRID 1869792Notes

Reaction equation

HRID 1869792 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].[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=1[N:34]=[C:35]=[O:36]>C(Cl)Cl>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=1[NH:34][C:35]([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:36]

Participants

4

Reactant 2

HCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 24755559Methyl 3-[2-(2,6-dichlorophenyl)quinolin-6-yl]alaninate

Product 1

HCID 68592692Methyl 2-{[(2,6-dichloroanilino)carbonyl]amino}-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoateYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.62 g of methyl 2-amino-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 33 in CH2Cl2 (10 ml) are added 0.343 g of 2,6-dichlorophenyl isocyanate. The solution is stirred at RT and reduced to the half by evaporation. The solid residue is filtered and washed with CH2Cl2 and hexane to give a white powder that is recrystallised in hot CH3CN. The compound is purified over silica gel using CH2Cl2/CH3OH 99.5/0.5 as eluent. The obtained white powder is once more washed with CH3CN to give methyl 2-{[(2,6-dichloroanilino)carbonyl]amino}-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 52.

Workup

  1. customreduced to the half by evaporation
  2. filtrationThe solid residue is filtered
  3. washwashed with CH2Cl2 and hexane
  4. customto give a white powder that
  5. customis recrystallised in hot CH3CN
  6. customThe compound is purified over silica gel
  7. washThe obtained white powder is once more washed with CH3CN

Sources & evidence

ORD record
ord-c2a9e1b7ff3c4fb6823c5b47e717acc5
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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