Dimethylformamide → HCID 68193064, compound

HRID 39779Notes

Reaction equation

HRID 39779 reaction equation
CN(C)C=O.Br[C:7]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11](=[O:46])[N:12]2[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([N:27]([CH2:35][C:36]2[CH:45]=[CH:44][C:39]3[O:40][CH2:41][CH2:42][O:43][C:38]=3[CH:37]=2)[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:23][CH2:22]1.[C:47]([O:51][CH2:52][CH3:53])(=[O:50])[CH:48]=[CH2:49]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C(N(CC)CC)C>[C:30]([O:29][C:28]([N:27]([CH2:35][C:36]1[CH:45]=[CH:44][C:39]2[O:40][CH2:41][CH2:42][O:43][C:38]=2[CH:37]=1)[CH:24]1[CH2:23][CH2:22][N:21]([CH2:20][CH2:19][N:12]2[C:13]3[C:8](=[C:7](/[CH:49]=[CH:48]/[C:47]([O:51][CH2:52][CH3:53])=[O:50])[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=3)[CH:9]=[CH:10][C:11]2=[O:46])[CH2:26][CH2:25]1)=[O:34])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8821Ethyl AcrylateHCID 59397948tert-butyl (1-(2-(5-bromo-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate

Product 1

HCID 68193064HCID 68193064, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

To 4.0 mL of an N,N-dimethylformamide solution containing 0.15 g of tert-butyl (1-(2-(5-bromo-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate, 39 μl of ethyl acrylate, 50 μL of triethylamine and 6.1 mg of bis(tri-tert-butylphosphine)palladium(0) were added and heated under nitrogen atmosphere at 90° C. for 1.5 hours. The reaction mixture was cooled to the room temperature, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=20:1] to give 0.15 g of ethyl (2E)-3-(1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate as a light brown foam.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was cooled to the room temperature
  3. customthe solvent was removed under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=20:1]

Sources & evidence

ORD record
ord-48f535a5c7464c48bb54cdbd7b3e232c
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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