Diisopropylethylamine → 4-[6-(3-Chloro-4-fluoro-phenyl)-2-(4-propyl-piperazin-1-yl)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1444135Notes

Reaction equation

HRID 1444135 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[N:17]=[C:16](Cl)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:29]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[CH2:30][CH3:31].CCN(C(C)C)C(C)C>CC(N(C)C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[N:17]=[C:16]([N:35]3[CH2:36][CH2:37][N:32]([CH2:29][CH2:30][CH3:31])[CH2:33][CH2:34]3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 415812Piperazine, 1-propyl-, hydrochloride (1:2)HCID 591683264-[2-Chloro-6-(3-chloro-4-fluoro-phenyl)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 591683134-[6-(3-Chloro-4-fluoro-phenyl)-2-(4-propyl-piperazin-1-yl)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Heat a solution of 4-[2-chloro-6-(3-chloro-4-fluoro-phenyl)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (2.5 g, 5.9 mmol), N-propylpiperazine (5.9 mmol) and DIEA (11.7 mmol) in DMA at 100° C. for 16 h. 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. temperatureCool
  2. custompartition between 10% NaOH and EtOAc
  3. washwash the organic layer with additional NaOH solution (3×)
  4. dry with materialDry the organic layer (Na2SO4)
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-cb4f3e8f5599451c9e795245638d995b
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

Loading…