Pyridine → HCID 19603320, compound

HRID 1604559Notes

Reaction equation

HRID 1604559 reaction equation
Cl[C:2]([O:5]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl.N1C=CC=CC=1.[Cl:19][C:20]1[C:38]([NH:39][CH3:40])=[CH:37][CH:36]=C(Cl)[C:21]=1[CH2:22][O:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[N:32]=[C:31]([CH3:34])[CH:30]=[CH:29]2.Cl.[CH2:43]([O:45][C:46](=[O:49])[CH2:47][NH2:48])[CH3:44].Cl[CH2:51][Cl:52]>O.C(N(CC)CC)C>[Cl:19][C:20]1[C:38]([N:39]([CH3:40])[C:2]([NH:48][CH2:47][C:46]([O:45][CH2:43][CH3:44])=[O:49])=[O:5])=[CH:37][CH:36]=[C:51]([Cl:52])[C:21]=1[CH2:22][O:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[N:32]=[C:31]([CH3:34])[CH:30]=[CH:29]2

Participants

8

Reactant 5

HCID 1049PyridineHCID 6344DichloromethaneHCID 94429TriphosgeneHCID 2723640Glycine ethyl ester, hydrochlorideHCID 19603332HCID 19603332, compound

Product 1

HCID 19603320HCID 19603320, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of bis(trichloromethyl)carbonate (232 mg), pyridine (273 mg) in dichloromethane was added 8-(2,6-dichloro-3-methylaminobenzyloxy)-2-methylquinoline (800 mg) at 0° C. under nitrogen atmosphere, and the mixture was stirred for 1 hour at ambient temperature. To the mixture were added glycine ethyl ester hydrochloride (289 mg) and triethylamine (582 mg), and the mixture was stirred for 3 hours at ambient temperature. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography (chloroform) to give 8-[2,6-dichloro-3-(N'-ethoxycarbonylmethyl-N-methylureido)benzyloxy]-2-methylquinoline (512 mg) as a powder.

Workup

  1. stirringthe mixture was stirred for 3 hours at ambient temperature
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (chloroform)

Sources & evidence

ORD record
ord-3a89640f73f9468882c701b6acb66499
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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