1-[2-[[2-[4-(5-Chloro-2-methoxyphenyl)piperazin-1-yl]ethyl]amino]pyrimidin-4-ylcarbonyl]piperidin-4-amine → HCID 178418621, compound

HRID 5343

Reaction equation

HRID 5343 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH3:33])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17]3[N:22]=[C:21]([C:23]([N:25]4[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]4)=[O:24])[CH:20]=[CH:19][N:18]=3)[CH2:10][CH2:9]2)[CH:7]=1.CS[C:36]1[NH:37][CH:38]=[CH:39][C:40](=[O:42])[N:41]=1>C1(C)C=CC=C(C)C=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH3:33])=[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][NH:16][C:17]3[N:22]=[C:21]([C:23]([N:25]4[CH2:26][CH2:27][CH:28]([NH:31][C:36]5[NH:37][CH:38]=[CH:39][C:40](=[O:42])[N:41]=5)[CH2:29][CH2:30]4)=[O:24])[CH:20]=[CH:19][N:18]=3)[CH2:12][CH2:13]2)[CH:7]=1

Participants

4

Reactant 2

HCID 197958671-[2-[[2-[4-(5-Chloro-2-methoxyphenyl)piperazin-1-yl]ethyl]amino]pyrimidin-4-ylcarbonyl]piperidin-4-amineHCID 178418670HCID 178418670, compound

Product 1

HCID 178418621HCID 178418621, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent2×

Procedure

2.3 g (4.9 mmol) of 1-[2-[[2-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]ethyl]amino]pyrimidin-4-ylcarbonyl]piperidin-4-amine, and 0.9 g (6.3 mmols) of 2-methylthiopyrimidin-4(1H)-one in solution in 40 ml of m-xylene are introduced into a 0.5 l, round bottomed flask and the mixture is heated at reflux of the m-xylene for 14 hours. The reaction mixture is cooled to room temperature and the solvent is then evaporated under reduced pressure. The crude product is purified by chromatography on a silica gel column (eluent: dichloromethane/methanol, 98/2 to 85/15) in order to obtain 1.56 g (2.74 mmols) of compound.

Workup

  1. temperaturethe mixture is heated
  2. customthe solvent is then evaporated under reduced pressure
  3. customThe crude product is purified by chromatography on a silica gel column (eluent: dichloromethane/methanol, 98/2 to 85/15) in order

Sources & evidence

ORD record
ord-d740cb40c09548b39dbf951d10f89106
Source dataset
uspto-grants-1993_09
Patent number
US05244894

Linked notes

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