Diisopropylethylamine → 1'-[6-(3-Chloro-4-fluoro-phenyl)-2-(4-propyl-piperazin-1-yl)-pyrimidin-4-yl]-3-methyl-5-nitro-1',2',3',4',5',6'-hexahydro-[2,4']bipyridinyl

HRID 2195072Notes

Reaction equation

HRID 2195072 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19]N[CH2:17][CH2:16]3)[N:12]=[C:11]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:22]3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl[C:31]1[C:36]([CH3:37])=[CH:35][C:34]([N+:38]([O-:40])=[O:39])=[CH:33][N:32]=1.[CH3:41]CN(C(C)C)C(C)C>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([N:21]3[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][CH3:29])[CH2:25][CH2:26]3)[N:12]=[C:13]([N:15]3[CH2:16][CH2:17][CH:41]([C:31]4[C:36]([CH3:37])=[CH:35][C:34]([N+:38]([O-:40])=[O:39])=[CH:33][N:32]=4)[CH2:19][CH2:20]3)[CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 896482-Chloro-3-methyl-5-nitropyridineHCID 591682494-(3-Chloro-4-fluoro-phenyl)-6-piperazin-1-yl-2-(4-propyl-piperazin-1-yl)-pyrimidine

Product 1

HCID 668391171'-[6-(3-Chloro-4-fluoro-phenyl)-2-(4-propyl-piperazin-1-yl)-pyrimidin-4-yl]-3-methyl-5-nitro-1',2',3',4',5',6'-hexahydro-[2,4']bipyridinyl

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Heat a mixture of 4-(3-chloro-4-fluoro-phenyl)-6-piperazin-1-yl-2-(4-propyl-piperazin-1-yl)-pyrimidine (300 mg, 0.72 mmol), 2-chloro-3-methyl-5-nitro-pyridine (149 mg, 0.86 mmol) and DIEA (186 mg, 1.44 mmol) in DMA (4 mL) for 16 h at 110° C. Cool, partition between 10% NaOH and EtOAc and wash the organic layer with additional NaOH solution (3×). Dry the organic layer (Na2SO4) and concentrate under reduced pressure to afford the title compound.

Workup

  1. temperatureHeat
  2. temperatureCool
  3. custompartition between 10% NaOH and EtOAc
  4. washwash the organic layer with additional NaOH solution (3×)
  5. dry with materialDry the organic layer (Na2SO4)
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-a79fd42413914181a5831485b7e6fe62
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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