Chloride → 7-[(3-Bromo-2-(2-cyanophenyl)benzofuran-5-yl)methylamino]-5-ethylpyrazolo[1,5-a]pyrimidine

HRID 1450413Notes

Reaction equation

HRID 1450413 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]#[N:18])=[C:8]([Br:19])[C:7]=2[CH:20]=1.Cl[C:22]1[N:27]2[N:28]=[CH:29][CH:30]=[C:26]2[N:25]=[C:24]([CH2:31][CH3:32])[CH:23]=1.[Cl-].C(N(CC)CC)C>C(O)C>[Br:19][C:8]1[C:7]2[CH:20]=[C:3]([CH2:2][NH:1][C:22]3[N:27]4[N:28]=[CH:29][CH:30]=[C:26]4[N:25]=[C:24]([CH2:31][CH3:32])[CH:23]=3)[CH:4]=[CH:5][C:6]=2[O:10][C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]#[N:18]

Participants

6

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 105354107-Chloro-5-ethylpyrazolo[1,5-a]pyrimidineHCID 199759705-(Aminomethyl)-3-bromo-2-(2-cyanophenyl)benzofuran

Product 1

HCID 199757637-[(3-Bromo-2-(2-cyanophenyl)benzofuran-5-yl)methylamino]-5-ethylpyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

540 mg (1.65 mmol) 5-(aminomethyl)-3-bromo-2-(2-cyanophenyl)benzofuran (prepared according to WO 92/09600) and 300 mg (1.65 mmol) 7-Chloro-5-ethylpyrazolo[1,5-a]pyrimidine (Example 1, Step B) were heated with reflux in 4 ml dry ethanol for 13 h. In order to complete the conversion of the amine 200 mg of the chloride and 0.24 ml triethylamine in 4 ml dry ethanol were added, and the mixture was heated for additional 21 h. The solvent was removed in vacuo, and the title compound isolated from the residue by chromatography (hexane/acetone 95:5 to 75:25) to give colorless crystals after evaporation to dryness,

Workup

  1. additionwere added
  2. temperaturethe mixture was heated for additional 21 h
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6cd0fa50b3f842329148b9d9b1c2c4a3
Source dataset
uspto-grants-1997_02
Patent number
US05602136

Reaction notes

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