Water → HCID 23144509, compound

HRID 1967788Notes

Reaction equation

HRID 1967788 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[S:7][C:8]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:17])=[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)=[O:4].[N:24]1[CH:29]=[CH:28][CH:27]=[N:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.O.C(=O)(O)[O-].[Na+]>C1COCC1>[O:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9]1[N:10]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:33]2[CH2:34][CH2:35][N:30]([C:25]3[N:24]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH2:31][CH2:32]2)[S:7][C:8]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 887471-(2-Pyrimidinyl)piperazine2×HCID 516892Sodium BicarbonateHCID 23144494HCID 23144494, compound

Product 1

HCID 23144509HCID 23144509, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 262 (300 mg, 0.860 mmol) was dissolved in THF (5.0 mL), and 1-(2-pyrimidinyl)piperazine (0.370 mL, 2.58 mmol) was added thereto, followed by stirring at room temperature for 16 hours. Further, 1-(2-pyrimidinyl)piperazine (0.370 mL, 2.58 mmol) was added to the reaction mixture, followed by stirring at room temperature for 2 hours. Water and aqueous saturated sodium bicarbonate solution were added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was purified through silica gel column chromatography (hexane:ethyl acetate=1:2) to afford the entitled Compound 278 (345 mg, 84%) as pale yellow crystals.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. filtrationthe precipitated solid was collected by filtration
  3. customThe resulting solid was purified through silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-260166a7f17142f6b09ee0dfa19132fe
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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