Bis(dimethylaminoethyl) ether → 7-Benzylamino-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 1026892Notes

Reaction equation

HRID 1026892 reaction equation
CN(CC[O:6][CH2:7]CN(C)C)C.C([Mg]Cl)(C)C.C1C[O:20]CC1.[CH2:22]([NH:29][C:30]1[N:35]2[N:36]=[CH:37][C:38](Br)=[C:34]2[N:33]=[CH:32][C:31]=1[C:40]([N:42]1[CH2:47][CH2:46][CH:45]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:44][CH2:43]1)=[O:41])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([NH:29][C:30]1[N:35]2[N:36]=[CH:37][C:38]([C:7]([OH:6])=[O:20])=[C:34]2[N:33]=[CH:32][C:31]=1[C:40]([N:42]1[CH2:47][CH2:46][CH:45]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:44][CH2:43]1)=[O:41])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 18204Bis(dimethylaminoethyl) etherHCID 675411767-Benzylamino-3-bromo-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidineHCID 178420664HCID 178420664, compound

Product 1

HCID 675405547-Benzylamino-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acidYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Bis[2-(N,N-dimethylamino)ethyl]ether (4.1 mL, 25.7 mmol) was dissolved in THF (15 mL), 2 mol/L isopropylmagnesium chloride-THF solution (13.0 mL, 25.7 mmol) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 5 min. A suspension (5 mL) of 7-benzylamino-3-bromo-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine (1.4 g, 2.9 mmol) obtained in step 4 in THF was added to this mixture under ice-cooling, and the mixture was stirred at room temperature for 2 hr. Carbon dioxide gas was bubbled into the reaction mixture for 30 min under ice-cooling, and the reaction mixture was added dropwise to ice-cooled 1 mol/L hydrochloric acid (100 mL). The mixture was stirred at room temperature for 1 hr, and the precipitate was collected by filtration, and washed with water (50 mL) to give the title compound (0.9 g, 67%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 2 hr
  4. customCarbon dioxide gas was bubbled into the reaction mixture for 30 min under ice-
  5. temperaturecooling
  6. additionthe reaction mixture was added dropwise to ice-
  7. temperaturecooled 1 mol/L hydrochloric acid (100 mL)
  8. stirringThe mixture was stirred at room temperature for 1 hr
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with water (50 mL)

Sources & evidence

ORD record
ord-08107ebc81634731a1c82c1d79856856
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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