HCID 13028015, compound → HCID 22617850, compound

HRID 842016Notes

Reaction equation

HRID 842016 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:20])[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[C:6]2[N:5]=[C:4]([CH3:21])[CH:3]=1.NCC[NH:25][C:26](=[O:36])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1>CN1CCCC1>[CH3:19][C:12]1[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=1[C:10]1[C:9]([CH3:20])=[N:8][N:7]2[C:2]([NH:25][C:26](=[O:36])[CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[CH:3][C:4]([CH3:21])=[N:5][C:6]=12

Participants

4

Reactant 2

HCID 13028015HCID 13028015, compoundHCID 22474364HCID 22474364, compound

Product 1

HCID 22617850HCID 22617850, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve 7-chloro-2,5-dimethyl-3-(2,4,6-trimethylphenyl)-pyrazolo[1,5-a]pyrimidine (0.26 g, 8.69×10−4 mol) in 2 mL N-methylpyrrolidine, and add N-(2-aminoethyl)-2-(4-methoxyphenyl)acetamide (0.75 g, 3.6 mmol). Heat to 80° C. overnight under N2. Partition between EtOAc (50 mL) and H2O (50 mL), then separate layers and wash EtOAC layer successively with 0.1 N NaOH (25 mL), H2O (25 mL), and brine. Pool aqueous layers and extract with EtOAc (25 mL). Pool EtOAc layers, dry over Na2SO4, filter and concentrate to yellow oil. Chromatograph on silica gel eluting with EtOAc and evaporate to obtain 0.30 g of N-(3-(2,4,6-trimethylphenyl)-2,5-dirnethyl-pyrazolo[1,5-a]pyrimidin-7yl)-2-(4-methoxyphenyl)acetamide as a clear pale yellow oil. LCMS=472.3 (MH+); 470.2 (M−). 1H-NMR (CDCl3): 7.10 (d, 2H, J=10.2 Hz); 6.39 (s, 2H); 6.81 (d, 2H, J=10.2 Hz); 6.46 (t, 1H, J=6.0 Hz); 6.16 (t, 1H, J=6.0 Hz); 5.79 (s, 1H); 3.76 (s, 3H); 3.45-3.50 (m, 6H); 2.38 (s, 3H); 2.30 (s, 3H); 2.20 (s, 3H); 2.02 (s, 6H).

Workup

  1. customPartition between EtOAc (50 mL) and H2O (50 mL)
  2. washseparate layers and wash EtOAC layer successively with 0.1 N NaOH (25 mL), H2O (25 mL), and brine
  3. extractionPool aqueous layers and extract with EtOAc (25 mL)
  4. dry with materialPool EtOAc layers, dry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate to yellow oil
  7. customChromatograph on silica gel eluting with EtOAc and evaporate

Sources & evidence

ORD record
ord-3f222a8e70364c6b888055eaa5b4509b
Source dataset
uspto-grants-2002_04
Patent number
US06372743B1

Reaction notes

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