Hydrochloric Acid → HCID 178519790, compound

HRID 1026889Notes

Reaction equation

HRID 1026889 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[C:10]([OH:11])=[C:9]([C:12]([OH:14])=O)[CH:8]=[N:7][C:6]=12.[C:15]1([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.C(OCC)(=O)C.Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[C:10]([OH:11])=[C:9]([C:12]([N:24]3[CH2:25][CH2:26][CH:21]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:22][CH2:23]3)=[O:14])[CH:8]=[N:7][C:6]=12

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 8857Ethyl Acetate2×HCID 698734-Phenylpiperidine2×HCID 178524688HCID 178524688, compound

Product 1

HCID 178519790HCID 178519790, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylic acid (6.3 g, 24.5 mmol) obtained in step 1 and 4-phenylpiperidine (7.9 g, 49.0 mmol) were suspended in methylene chloride (120 mL), triethylamine (13.7 ml, 98.1 mmol) and 50% 1-propylphosphonic acid anhydride cyclic trimer-ethyl acetate solution (6.0 g, 49.0 mmol) were added at 0° C., and the mixture was stirred at 0° C. for 2 hr. 4-Phenylpiperidine (7.9 g, 49.0 mmol), triethylamine (13.7 mL, 98.1 mmol) and 50% 1-propylphosphonic acid anhydride cyclic trimer-ethyl acetate solution (6.0 g, 49.0 mmol) were added to the reaction mixture, and the mixture was further stirred at 0° C. for 2 hr. 2 mol/L Hydrochloric acid (100 mL) was added to the reaction mixture, the organic layer and the aqueous layer were separated, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 2 mol/L Hydrochloric acid (100 mL) was added to the residue, and the mixture was stirred at 30° C. for 2 hr. The precipitate was collected by filtration, and washed with water (100 mL) to give the title compound (7.7 g, 78%).

Workup

  1. stirringthe mixture was further stirred at 0° C. for 2 hr
  2. customthe organic layer and the aqueous layer were separated
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. addition2 mol/L Hydrochloric acid (100 mL) was added to the residue
  6. stirringthe mixture was stirred at 30° C. for 2 hr
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water (100 mL)

Sources & evidence

ORD record
ord-58e8986a9ba84f10a67ac771fd8eaa83
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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