Diisoamylamine → HCID 68277118, compound

HRID 1475946Notes

Reaction equation

HRID 1475946 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:20]=[C:12]3[N:13]=[C:14]([C:17]([OH:19])=O)[CH:15]=[CH:16][N:11]3[N:10]=2)=[CH:5][CH:4]=1.[CH2:21]([NH:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:22][CH:23]([CH3:25])[CH3:24].O.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(Cl)Cl.[Cl-].[NH4+].O.CO>[CH2:27]([N:26]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]([C:14]1[CH:15]=[CH:16][N:11]2[N:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH:20]=[C:12]2[N:13]=1)=[O:19])[CH2:28][CH:29]([CH3:30])[CH3:31]

Participants

10

Reactant 4

HCID 10988DiisoamylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 68276036HCID 68276036, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 68277118HCID 68277118, compoundYield 89%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 2-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine-5-carboxylic acid in DMF (10 mL) and methylene chloride (5 mL) was added diisopentylamine (0.67 mL; 512 mg; 3.3 mmol) and hydroxybenzotriazole monohydrate (499 mg; 3.3 mmol). The mixture was stirred for 10 min. at room temperature and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (626 mg; 3.3 mmol) was added. The mixture was stirred overnight at room temperature. An additional amount of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride was then added (626 mg; 3.3 mmol) and the reaction mixture was heated to 50° C. for 30 min. The mixture was then cooled to room temperature, diluted with methylene chloride and saturated ammonium chloride was added. The aqueous layer was back extracted with methylene chloride and the combined organics were washed with water (3×10 mL) and brine. Concentration afforded a crude oil that was purified by flash-chromatography using first 100% methylene chloride then 5% methanol in methylene chloride to afford an oil that solidified under vacuum. This solid was taken into hot methanol (7 mL) and, upon cooling, a solid formed. Water (3 mL) was then added slowly and filtration afforded 590 mg (89%) of the title compound. LCMS m/z 409.3 (M+H)+, ret. time=3.08 min.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. temperaturethe reaction mixture was heated to 50° C. for 30 min
  3. temperatureThe mixture was then cooled to room temperature
  4. additionwas added
  5. extractionThe aqueous layer was back extracted with methylene chloride
  6. washthe combined organics were washed with water (3×10 mL) and brine
  7. concentrationConcentration
  8. customafforded a crude oil that
  9. customwas purified by flash-chromatography
  10. custom5% methanol in methylene chloride to afford an oil that
  11. temperatureupon cooling
  12. customa solid formed
  13. filtrationfiltration

Sources & evidence

ORD record
ord-6c79a19eca3d464887a117fbe42d88a6
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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