1-Ethylpiperazine → HCID 59507055, compound

HRID 1800598Notes

Reaction equation

HRID 1800598 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[S:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[C:10]([O:15][C:16]1[CH:17]=[C:18]([NH:23][C:24](=[O:36])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([C:34]#[N:35])([CH3:33])[CH3:32])[CH:26]=3)[CH:19]=[CH:20][C:21]=1[CH3:22])[N:9]=2)=[O:4].[CH2:37]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[CH3:38].C(=O)([O-])O.[Na+]>O1CCCC1>[C:34]([C:31]([C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[C:24]([NH:23][C:18]1[CH:19]=[CH:20][C:21]([CH3:22])=[C:16]([O:15][C:10]2[N:9]=[C:8]3[S:7][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:42]4[CH2:43][CH2:44][N:39]([CH2:37][CH3:38])[CH2:40][CH2:41]4)=[N:14][C:13]3=[CH:12][CH:11]=2)[CH:17]=1)=[O:36])([CH3:32])[CH3:33])#[N:35]

Participants

5

Reactant 3

HCID 791961-EthylpiperazineHCID 516892Sodium BicarbonateHCID 86646041HCID 86646041, compound

Product 1

HCID 59507055HCID 59507055, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-[3-({2-[(chloroacetyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]-3-(1-cyano-1-methylethyl)benzamide (284 mg, 0.547 mmol) produced in Example C15(i), 1-ethylpiperazine (114 μL, 0.901 mmol) triethylamine (125 μL, 0.901 mmol) and tetrahydrofuran (5 mL) was stirred at 60° C. for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and filtered through a pad filled with basic silica gel. The filtrate was concentrated under reduced pressure, and the obtained residue was recrystallized from ethyl acetate to give the title compound (138 mg, 51%) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered through a pad
  5. additionfilled with basic silica gel
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-aaa6aadb3ac24ddeafb7371c888c879b
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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