1-(4-(4-aMino-3-Methoxyphenyl)piperazin-1-yl)ethanone → HCID 72546716, compound

HRID 1496971Notes

Reaction equation

HRID 1496971 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:17][CH3:18].Cl[C:20]1[N:25]=[C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][N:36]([C:39](=[O:41])[CH3:40])[CH2:35][CH2:34]3)=[CH:29][C:28]=2[O:42][CH2:43][CH3:44])[C:23]([Cl:45])=[CH:22][N:21]=1>C(OC(O)C)C.Cl>[C:39]([N:36]1[CH2:35][CH2:34][N:33]([C:30]2[CH:31]=[CH:32][C:27]([NH:26][C:24]3[C:23]([Cl:45])=[CH:22][N:21]=[C:20]([NH:1][C:2]4[CH:7]=[CH:6][C:5]([N:8]5[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH2:9]5)=[CH:4][C:3]=4[O:17][CH3:18])[N:25]=3)=[C:28]([O:42][CH2:43][CH3:44])[CH:29]=2)[CH2:38][CH2:37]1)(=[O:41])[CH3:40]

Participants

4

Reactant 2

HCID 552327371-(4-(4-aMino-3-Methoxyphenyl)piperazin-1-yl)ethanoneHCID 118105738HCID 118105738, compound

Product 1

HCID 72546716HCID 72546716, compound

Reagents, catalysts & solvents 1

HCID 19698338HCID 19698338, compoundSolvent

Procedure

1-(4-(4-amino-3-methoxyphenyl)piperazin-1-yl)ethanone (40 mg) prepared in Preparation Example 1 and 1-(4-(4-(2,5-dichloropyrimidine-4-ylamino)-3-ethoxyphenyl)piperazin-1-yl)ethanone (50 mg) prepared in Preparation Example 15 were dissolved in 0.08M HCl ethoxyethanol solution (1.2 mL), and allowed to react at 115° C. overnight. Upon completion of the reaction, the solvent of the mixture was removed under reduced pressure, diluted with ethyl acetate, neutralized with an aqueous saturated sodium carbonate solution, water was removed from the organic layer with sodium sulfate, and the solvent was removed under reduced pressure. The mixture was purified by column chromatography to obtain a target compound.

Workup

  1. customprepared in Preparation Example 15
  2. customto react at 115° C. overnight
  3. customUpon completion of the reaction
  4. customthe solvent of the mixture was removed under reduced pressure
  5. additiondiluted with ethyl acetate
  6. customwas removed from the organic layer with sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe mixture was purified by column chromatography
  9. customto obtain a target compound

Sources & evidence

ORD record
ord-38dfc35b5e5d4bbeacce2517d28a0079
Source dataset
uspto-grants-2015_12
Patent number
US09199944B2

Reaction notes

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