Pyridine → HCID 54053710, compound

HRID 1857640Notes

Reaction equation

HRID 1857640 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][S:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:31])=[C:27]([NH2:30])[CH:28]=2)[NH:23][C:22](=[O:32])[C:21]=1[C:33]1[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:41]1[CH:46]=C[CH:44]=[CH:43][CH:42]=1.C(Cl)(Cl)=[O:48].C1(N)CC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][S:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:31])=[C:27]([NH:30][C:46]([NH:41][CH:42]3[CH2:44][CH2:43]3)=[O:48])[CH:28]=2)[NH:23][C:22](=[O:32])[C:21]=1[C:33]1[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 69828CyclopropylamineHCID 53986725HCID 53986725, compound

Product 1

HCID 54053710HCID 54053710, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-ylsulfanyl]-ethyl }-piperidine-1-carboxylic acid benzyl ester (23 mg in 1.0 mL methylene chloride) at 0° C. was added 0.01 mL pyridine followed by phosgene (0.03 mL of a 1.93M solution in toluene) and the mixture allowed to stir at 0° C. for 1 hour. At this time 0.02 mL of cyclopropylamine was added via syringe and the reaction mixture warmed to room temperature. After 4 hours, the mixture was diluted with ethyl acetate and washed sequentially with 10% aqueous sodium bisulfate, water and brine. The organic portion was dried over magnesium sulfate then concentrated in vacuo. Purification of the crude material by flash chromatography on silica gel (chloroform:methanol, 95:5) gave the title compound (18 mg).

Workup

  1. temperaturethe reaction mixture warmed to room temperature
  2. waitAfter 4 hours
  3. washwashed sequentially with 10% aqueous sodium bisulfate, water and brine
  4. dry with materialThe organic portion was dried over magnesium sulfate
  5. concentrationthen concentrated in vacuo
  6. customPurification of the crude material by flash chromatography on silica gel (chloroform:methanol, 95:5)

Sources & evidence

ORD record
ord-81040d6c3cae43c58773b3d7a12f8f2e
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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