Triethylamine → HCID 53882044, compound

HRID 1604590Notes

Reaction equation

HRID 1604590 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.[C:47](Cl)(=[O:51])[CH:48]([CH3:50])[CH3:49]>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:47](=[O:51])[CH:48]([CH3:50])[CH3:49])=[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 62325Isobutyryl chlorideHCID 53932501HCID 53932501, compound

Product 1

HCID 53882044HCID 53882044, compoundYield 86.7%

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 isobutyryl chloride (41.6 mg) at 0° C. under nitrogen atmosphere, and the mixture was stirred for 30 minutes at the same temperature. The mixture was concentrated, and the residue was dissolved in methanol (3 ml). To the solution was added saturated sodium bicarbonate solution (1 ml), and the mixture was stirred for 2 hours at ambient temperature and concentrated. To the residue were added ethyl acetate and water, and the organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried and concentrated. 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-(4-isobutyramido-3-methylcinnamoylglycyl)amino]benzyloxy]-2-methylquinoline (195 mg) as an amorphous powder.

Workup

  1. customat 0° C.
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in methanol (3 ml)
  4. additionTo the solution was added saturated sodium bicarbonate solution (1 ml)
  5. stirringthe mixture was stirred for 2 hours at ambient temperature
  6. concentrationconcentrated
  7. additionTo the residue were added ethyl acetate and water
  8. washthe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  9. customdried
  10. concentrationconcentrated
  11. customThe residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=15:1, V/V)

Sources & evidence

ORD record
ord-71bde3d06cd94bcdb5ea28d91179e69a
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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