Triethylamine → HCID 16723143, compound

HRID 1929737Notes

Reaction equation

HRID 1929737 reaction equation
[ClH:1].[NH2:2][N:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.O.ON1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2N=N1.[ClH:19].CN(C)[CH2:22][CH2:23][CH2:24][N:25]=[C:26]=[N:27][CH2:28][CH3:29].[C:31](=[O:34])([O-])O.[Na+].C([N:38]([CH2:41][CH3:42])CC)C>C(Cl)(Cl)Cl.O>[Cl:1][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:29]1[CH:28]=[N:27][C:26]2[N:25]([N:38]=[CH:41][C:42]=2[C:31](=[O:34])[NH:2][N:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)[C:24]=1[C:23]1[CH:22]=[CH:7][C:6]([Cl:19])=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 3017392Pyrrolidin-1-amine monohydrochloride

Product 1

HCID 16723143HCID 16723143, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of the compound obtained in Reference Example 1 (57.6 mg) and 1-aminopyrrolidine HCl (24.5 mg) in chloroform (1.0 mL containing amylene) was added 1-hydroxybenzotriazole monohydrate (0.23 mL, 0.5M chloroform solution containing amylene), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl (0.23 mL, 0.5M N,N-dimethylformamide solution) and triethylamine (63 μL) and the mixture was stirred at room temperature overnight. To the reaction mixture was added an aqueous saturated sodium hydrogencarbonate solution (2 mL), water (2 mL) and chloroform (5 mL) and the mixture was stirred vigorously for 15 minutes. After separating the organic layer, the aqueous layer was extracted with chloroform (3 mL). The combined organic layer was washed successively with an aqueous saturated sodium hydrogencarbonate solution (3 mL) and saturated brine (3 mL) and concentrated in vacuo. The resultant crude product was purified by liquid chromatograph-mass spectrometer (LCMS) (column; XTerra MS C18, solvent; 10 mM ammonium carbonate/methanol=40/60 to 10/90). The eluted fraction was concentrated and the residue was dissolved in tert-buthanol and lyophilized to give 6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-(N-pyrrolidinocarbamoyl)pyrazolo[1,5-a]pyrimidine (47.2 mg; yield: 70%) as a powder.

Workup

  1. stirringthe mixture was stirred vigorously for 15 minutes
  2. customAfter separating the organic layer
  3. extractionthe aqueous layer was extracted with chloroform (3 mL)
  4. washThe combined organic layer was washed successively with an aqueous saturated sodium hydrogencarbonate solution (3 mL) and saturated brine (3 mL)
  5. concentrationconcentrated in vacuo
  6. customThe resultant crude product was purified by liquid chromatograph-mass spectrometer (LCMS) (column; XTerra MS C18, solvent; 10 mM ammonium carbonate/methanol=40/60 to 10/90)
  7. concentrationThe eluted fraction was concentrated
  8. dissolutionthe residue was dissolved in tert-buthanol

Sources & evidence

ORD record
ord-e663deb7d43c4893ad01310d31c0dc27
Source dataset
uspto-grants-2012_05
Patent number
US08188097B2

Reaction notes

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