Diisopropylethylamine → HCID 178523062, compound

HRID 606383Notes

Reaction equation

HRID 606383 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14]CC)=O)[NH:3]1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:24]2[CH:28]=[N:27][C:26]([CH2:29][CH2:30][CH2:31][O:32][C:33]3[CH:38]=[C:37]([CH2:39][NH2:40])[CH:36]=[CH:35][N:34]=3)=[N:25]2)C=CC=CC=1.C(N(C(C)C)CC)(C)C>C(O)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:40][CH2:39][C:37]2[CH:36]=[CH:35][N:34]=[C:33]([O:32][CH2:31][CH2:30][CH2:29][C:26]3[N:27]=[CH:28][NH:24][N:25]=3)[CH:38]=2)=[O:14])[NH:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 667687691-[2-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propyl}oxy)pyridin-4-yl]methanamineHCID 135437466Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 178523062HCID 178523062, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate obtained according to the methods described in Journal of Organic Chemistry (1978), 43(23), 4485-7 and the like (25.0 mg, 0.11 mmol), 1-[2-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propyl}oxy)pyridin-4-yl]methanamine obtained in Reference Example 28 (28.0 mg, 0.069 mmol) and diisopropylethylamine (159 mg, 1.20 mmol) in ethanol (3 mL) was stirred at 80° C. for 15 hr. After cooling the mixture to room temperature, the resulting solid was collected by filtration, and washed with ethanol. 4N Hydrochloric acid and ethyl acetate were added to the crude crystals, and the mixture was stirred at room temperature for 2 hr. Water was added to the mixture, and the aqueous layer was weakly acidified with saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The obtained crude crystals were recrystallized from ethanol to give the title compound as a white powder (28.0 mg, 60%).

Workup

  1. customobtained
  2. temperatureAfter cooling the mixture to room temperature
  3. filtrationthe resulting solid was collected by filtration
  4. washwashed with ethanol
  5. addition4N Hydrochloric acid and ethyl acetate were added to the crude crystals
  6. stirringthe mixture was stirred at room temperature for 2 hr
  7. additionWater was added to the mixture
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customThe obtained crude crystals
  13. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-9bad3f7e250e44119d319d7f3663254a
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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