Triethylamine → 2-{4-[(2-Phenylimidazol-5-yl)methyl]piperazinyl}quinazoline

HRID 1276597Notes

Reaction equation

HRID 1276597 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH2:12]O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[N:16][C:15]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)CC)C>S(Cl)(Cl)=O>[C:1]1([C:7]2[NH:11][C:10]([CH2:12][N:27]3[CH2:28][CH2:29][N:24]([C:15]4[N:16]=[CH:17][C:18]5[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=5)[N:14]=4)[CH2:25][CH2:26]3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64232662-Piperazin-1-yl-quinazolineHCID 10080865(2-Phenyl-1H-imidazol-5-yl)methanol

Product 1

HCID 99293032-{4-[(2-Phenylimidazol-5-yl)methyl]piperazinyl}quinazolineYield 86.4%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A sample of 2-phenyl-4-hydroxymethylimidazole (348 mg, 2 mmol) is heated for 5 min in thionyl chloride (5 mL) and subsequently concentrated. Chloroform (10 mL) is added and the solution reconcentrated. The resulting dark oil is then taken up in chloroform (10 mL) and treated with 1-quinazolin-2-ylpiperazine (428 mg, 2 mmol) and triethyl amine (2 mL). After 10 minutes, the reaction is washed with 2N NaOH solution, dried (Na2SO4) and concentrated to provide the title compound (Compound 4) as an oil (640 mg), the hydrochloride salt is prepared in a conventional manner, m.p. 101-105° C. (Compound 4a). 1H NMR (CDCl3) 9.0 (s, 1H), 7.9 (d, J=7 Hz, 2H), 7.65 (m, 2H), 7.55 (d, J=6 Hz, 1H), 7.2-7.4 (m, 4H), 7.0 (s, 1H, imidazole CH), 3.95 (m, 4H), 3.6 (s, 2H), 2.6 (t, J=5 Hz, 4H).

Workup

  1. concentrationsubsequently concentrated
  2. additionChloroform (10 mL) is added
  3. washthe reaction is washed with 2N NaOH solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eddf2b4297e94ff8952007cd734576bb
Source dataset
uspto-grants-2000_12
Patent number
US06166205

Reaction notes

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