N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(phenylmethoxy)-4-quinazolinamine synthesis
- Product Name:N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(phenylmethoxy)-4-quinazolinamine
- CAS Number:913819-12-2
- Molecular formula:C22H17ClFN3O2
- Molecular Weight:409.84
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Yield:913819-12-2 54 g
Reaction Conditions:
with N-ethyl-N,N-diisopropylamine in isopropyl alcohol at 60 - 65; for 2 h;
Steps:
Preparation of 4-(3-chloro-4-flurophenylamino)-6-benzoyloxy-7-methoxy quinazoline, 11.
Oxalylchloride (62.9 g, 0.496 mol) was added to a mixture of 6-benzyloxy-7-methoxyquinazolin-4(3H)-one 9 (40 g, 0.1416 mol) and diisopropyl ethyl amine (21 g, 0.1625 mol) in chloroform 200 mL. The reaction was maintained at 60-65°C for 12 hr. The solvent was completely removed by vacuum distillation. A solution of 3-chloro-4-fluoroaniline (28.7 g, 0.1982 mol) in isopropanol 480 mL was added to the reaction mass at 25-30°C. The reaction mass was heated up to 60-65°C followed by slow addition of diisopropylamine (21 g, 0.1625 mol) and maintaining for 2 hr. The mixture was cooled to 0-5°C for a period of 1 hr. The solid was collected by filtration, washed with chilled isopropanol and dried to get the light yellow compound 11 (54 g, 93%), purity 98-99% m.p. 258-60°C; 1H NMR (Methanol-d4, 300 MHz): δ 8.183 (s, 1H), 8.005-8.036 (m, 1H), 7.709-7.761 (m, 1H), 7.556-7.602 (m, 2H), 7.378-7.531 (m, 5H), 7.321 (s, 1 H), 5.380 (s, 2H), 4.153 (s, 3H); MS (EI): m/z 411 (M + 1).
References:
Kumar, Neeraj;Chowdhary, Anil;Gudaparthi, Omprakash;Patel, Nilesh G.;Soni, Sanjay K.;Sharma, Pradeep [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2014,vol. 53B,# 10,p. 1269 - 1274]
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