Dimethylformamide → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(pyrimidin-4-ylcarbamoyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1858092Notes

Reaction equation

HRID 1858092 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:28])=[C:24](I)[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][N:40]=1.CN(C)[CH:47]=[O:48]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:28])=[C:24]([C:47](=[O:48])[NH:38][C:39]3[CH:44]=[CH:43][N:42]=[CH:41][N:40]=3)[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 689584-AminopyrimidineHCID 539972552-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-iodo-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 537223102-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(pyrimidin-4-ylcarbamoyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-iodo-2-oxo -1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (0.10 g in a mixture of 1 mL N,N-dimethylformamide and 0.04 mL triethylamine) was added 75 mg of 4-aminopyrimidine followed by 0.8 mg dichlorobis(triphenylphosphine)palladium(II) and the flask flushed (5×) with carbon monoxide. The mixture was then heated to 90° C. on an oil bath under a carbon monoxide atmosphere. After 16 hours, the mixture was cooled to room temperature, diluted with ethyl acetate and washed with water and brine. The organic portion was dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel (ethyl acetate:hexane, 35:65; then methylene chloride:methanol, 95:5) gave the title compound (70 mg).

Workup

  1. customthe flask flushed (5×) with carbon monoxide
  2. temperaturethe mixture was cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic portion was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-abb56d654a5c4ba1b1e452b9c519ddaf
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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