Triethylamine → HCID 54285081, compound

HRID 1604592Notes

Reaction equation

HRID 1604592 reaction equation
[NH2:1][C:2]1[CH:38]=[CH:37][C:5]([CH:6]=[CH:7][C:8]([NH:10][CH2:11][C:12]([N:14]([C:16]2[C:17]([Cl:36])=[C:18]([C:32]([Cl:35])=[CH:33][CH:34]=2)[CH2:19][O:20][C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]=2[N:29]=[C:28]([CH3:31])[CH:27]=[CH:26]3)[CH3:15])=[O:13])=[O:9])=[CH:4][C:3]=1[CH3:39].C(N(CC)CC)C.[CH3:47][N:48]=[C:49]=[O:50]>ClCCl>[Cl:36][C:17]1[C:16]([N:14]([CH3:15])[C:12](=[O:13])[CH2:11][NH:10][C:8](=[O:9])[CH:7]=[CH:6][C:5]2[CH:37]=[CH:38][C:2]([NH:1][C:49]([NH:48][CH3:47])=[O:50])=[C:3]([CH3:39])[CH:4]=2)=[CH:34][CH:33]=[C:32]([Cl:35])[C:18]=1[CH2:19][O:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([CH3:31])[CH:27]=[CH:26]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl Isocyanate2×HCID 53932501HCID 53932501, compound

Product 1

HCID 54285081HCID 54285081, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-[3-[N-(4-amino-3-methylcinnamoylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (200 mg) and triethylamine (35.9 mg) in dichloromethane was dropwise added methyl isocyanate (0.023 ml) at 0° C. under nitrogen atmosphere, and the mixture was stirred for 1 hour at the same temperature and for 2 hours at ambient temperature. Methyl isocyanate (0.03 ml) was further added thereto, and the mixture was stirred overnight at ambient temperature. The mixture was partitioned between dichloromethane and water, the organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=15:1, V/V) to give 8-[2,6-dichloro-3-[N-methyl-N-[3-methyl-4-(N'-methylureido)cinnamoylglycyl]amino]benzyloxy]-2-methylquinoline (150 mg) as an amorphous powder.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred overnight at ambient temperature
  3. customThe mixture was partitioned between dichloromethane and water
  4. washthe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=15:1, V/V)

Sources & evidence

ORD record
ord-c5c11f292ee042f2a1780b094d2a3bfe
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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