3-Pentanamine → HCID 9968298, compound

HRID 2183536Notes

Reaction equation

HRID 2183536 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.[CH2:22]([CH:24]([NH2:27])[CH2:25][CH3:26])[CH3:23]>CN1CCCC1=O>[CH3:20][C:9]1[C:10]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])=[C:6]2[N:5]=[C:4]([CH3:21])[CH:3]=[C:2]([NH:27][CH:24]([CH2:25][CH3:26])[CH2:22][CH3:23])[N:7]2[N:8]=1

Participants

4

Reactant 2

HCID 120193-PentanamineHCID 22474364HCID 22474364, compound

Product 1

HCID 9968298HCID 9968298, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 7-Chloro-2,5-dimethyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (60 mg, 0.2 mmol) and 1-ethylpropylamine (4 ml) in 1 ml of N-methylpyrro-lidinone was heated at 125° C. oil bath for 15 hrs. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated and purified through silica gel column chromatography using 20% ethyl acetate in hexane as eluent to give 35 mg of the title compound as a yellow solid. 1H NMR (CDCl3) ä 6.96(s, 2H), 6.00(d, 1H), 5.77(s, 1)H, 3.47 (m, 1H), 2.43(s, 3H), 2.32(s, 3H), 2.22(s, 3H), 2.05(s, 6H), 1.5-1.9(m, 4H), 1.04(t, 6H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. custompurified through silica gel column chromatography

Sources & evidence

ORD record
ord-94c5a8cdf4834787a2daa7e28674f343
Source dataset
uspto-grants-2005_05
Patent number
US06900217B2

Reaction notes

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