Nitrogen → HCID 19379860, compound

HRID 1109747Notes

Reaction equation

HRID 1109747 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=O)[CH:7](C(OC)=O)[N:8]2[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[Mg+2].[Cl-].[Cl-].N#N.[CH3:28][CH:29]([N:31]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[C:32]1=[O:44])[CH3:30].[NH4+].[Cl-]>CN1C(=O)CCC1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:41]3[CH2:42][CH2:43][N:38]([CH2:37][CH2:36][N:33]4[CH2:34][CH2:35][N:31]([CH:29]([CH3:28])[CH3:30])[C:32]4=[O:44])[CH2:39][CH2:40]3)=[CH:7][N:8]2[C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 5360315Magnesium ChlorideHCID 19379838HCID 19379838, compoundHCID 19379879HCID 19379879, compound

Product 1

HCID 19379860HCID 19379860, compoundYield 50.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
130 °C

Procedure

To 6-chloro-2-methoxycarbonyl-1-(4-fluorophenyl)-3-indolinon (7.5 g) in NMP (75 ml) was added MgCl2, 6H2O (9 g). The mixture was heated at 130° C. under N2 for one hour and finally the temperature was raised to 190° C. while H2O vapours were carried away by a gentle stream of N2. 1-[2-[3-(2-propyl)-2-imidazolidinon-1-yl]ethyl]-piperazine (12 g) in NMP (30 ml) were added and the temperature kept at 190°-200° C. for another hour. After cooling to room temperature the reaction mixture was poured into ethyl acetate (200 ml) and a saturated NH4Cl solution (500 ml) added. The organic phase was separated, dried (anh. MgSO4), filtered and the solvent evaporated. The remaining oil was purified by column chromatography on silica gel (eluent ethyl acetate/ethanol/triethylamine 90/10/4) yielding 5.7 g of pure title compound 6a. Mp: 176° -177° C.

Workup

  1. waitthe temperature kept at 190°-200° C. for another hour
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. customThe organic phase was separated
  4. dry with materialdried (anh. MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe remaining oil was purified by column chromatography on silica gel (eluent ethyl acetate/ethanol/triethylamine 90/10/4)

Sources & evidence

ORD record
ord-191f4ddb15c5439880e81ef506cae653
Source dataset
uspto-grants-1994_06
Patent number
US05322851

Reaction notes

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