3-[(4-METHYLBENZYL)AMINO]PROPAN-1-OL → HCID 15521237, compound

HRID 324369Notes

Reaction equation

HRID 324369 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]2[N:9]([C:14]3[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=3[Cl:22])[N:10]=[C:11]([S:12][CH3:13])[C:3]=12.[CH3:23][C:24]1[CH:35]=[CH:34][C:27]([CH2:28][NH:29][CH2:30][CH2:31][CH2:32][OH:33])=[CH:26][CH:25]=1>C(#N)C>[CH3:23][C:24]1[CH:35]=[CH:34][C:27]([CH2:28][N:29]([C:2]2[N:7]=[C:6]([CH3:8])[N:5]=[C:4]3[N:9]([C:14]4[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[CH:16][C:15]=4[Cl:22])[N:10]=[C:11]([S:12][CH3:13])[C:3]=23)[CH2:30][CH2:31][CH2:32][OH:33])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 32642233-[(4-METHYLBENZYL)AMINO]PROPAN-1-OLHCID 15521236HCID 15521236, compound

Product 1

HCID 15521237HCID 15521237, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-3-methylsulfanyl-6-methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine (788 mg, 2 mmol) and 3-(p-methylbenzyl)amino-1-propanol (716 mg, 4 mmol) in 10 ml of acetonitrile was heated at reflux for 4 hours. The mixture was cooled, quenched with water and dilute hydrogen chloride and extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate and brine, separated, dried and concentrated to give 953 mg of the title compound as an off-white glass form. The material was purified through silica gel column chromatography using chloroform as eluent to give the title compound as a white glass form. 1H NMR (CDCl3): 1.79 (m, 2H), 2.38 (s, 3H), 2.52 (s, 3H), 2.54 (s, 3H), 3.56 (t, 2H), 3.86 (t, 2H), 5.12 (s, 2H), 7.20 (s, 4H), 7.51 (s,2H) ppm. 13C NMR (CDCl3): 16.20, 21.13, 25.53, 29.64, 43.51, 53.88, 58.24, 127.78, 128.77, 129.33, 133.51, 136.18, 137.41, 142.93, 159.13, 164.89 ppm. IR(KBr): 3350, 2935, 1540 cm−1. Anal. calc. for C24H24N5OSCl3: C, 53.69; H, 4.50; N, 13.04; found: C, 53.33, H, 4.44, N, 12.84.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. customquenched with water and dilute hydrogen chloride
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with aqueous sodium bicarbonate and brine
  7. customseparated
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-66e443798b9a4331a1f56bcc18b46104
Source dataset
uspto-grants-2001_04
Patent number
US06218397B1

Reaction notes

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