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【结 构 式】

【分子编号】23776

【品名】2,3-dimethoxy-5-[(9-methoxy-6,6-dimethyl-5,6-dihydrobenzo[h]quinazolin-2-yl)amino]phenol

【CA登记号】

【 分 子 式 】C23H25N3O4

【 分 子 量 】407.46932

【元素组成】C 67.8% H 6.18% N 10.31% O 15.71%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XI)

Condensation of anisole (I) with gamma,gamma-dimethylbutyrolactone (II) in the presence of AlCl3 in 1-nitropropane gave 4-(4-methoxyphenyl)-4-methylpentanoic acid (III), which was cyclized to the tetralone (V) using polyphosphoric acid. Subsequent treatment of (V) with refluxing N,N-dimethylformamide dimethyl acetal provided the dimethylamino-methylene compound (VI). This was cyclized with guanidinium carbonate in boiling isopropanol to furnish the benzoquinazoline (VII). Then, diazotization of (VII) in aqueous sulfuric acid generated the quinazolinone (VIII), which was subsequently converted to chloroquinazoline (IX) with phosphoryl chloride in the presence of DMF. Condensation of (IX) with aniline (X) in refluxing ethoxyethanol gave (XI). Finally, the hydroxyl group of (XI) was alkylated with (diethylamino)ethyl chloride (XII) in the presence of Cs2CO3 in DMF at 110 C to yield the title compound.

1 Davis, J.M.; Hutchings, M.C.; Moffat, D.; Batchelor, M.; Parry, D.M.; Johnson, J.; Berg, D.A.; Davis, P.D.; Benzo[h]-5,6-dihydroquinazoline-2-amines as potent. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.234.
2 Moffat, D.F.C.; Davis, J.M.; Batchelor, M.J.; Davis, P.D. (Celltech Chiroscience plc); Fused polycyclic 2-aminopyrimidine derivs., their . EP 0946523; US 6057329; WO 9828281 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 23767 Methoxybenzene; Methyl phenyl ether; Anisole 100-66-3 C7H8O 详情 详情
(II) 23768 5,5-dimethyldihydro-2(3H)-furanone C6H10O2 详情 详情
(III) 23769 4-(4-methoxyphenyl)-4-methylpentanoic acid 23203-48-7 C13H18O3 详情 详情
(V) 23770 7-methoxy-4,4-dimethyl-3,4-dihydro-1(2H)-naphthalenone C13H16O2 详情 详情
(VI) 23771 2-[(E)-(dimethylamino)methylidene]-7-methoxy-4,4-dimethyl-3,4-dihydro-1(2H)-naphthalenone C16H21NO2 详情 详情
(VII) 23772 9-methoxy-6,6-dimethyl-5,6-dihydrobenzo[h]quinazolin-2-ylamine; 9-methoxy-6,6-dimethyl-5,6-dihydrobenzo[h]quinazolin-2-amine C15H17N3O 详情 详情
(VIII) 23773 9-methoxy-6,6-dimethyl-5,6-dihydrobenzo[h]quinazolin-2(1H)-one C15H16N2O2 详情 详情
(IX) 23774 2-chloro-6,6-dimethyl-5,6-dihydrobenzo[h]quinazolin-9-yl methyl ether; 2-chloro-9-methoxy-6,6-dimethyl-5,6-dihydrobenzo[h]quinazoline C15H15ClN2O 详情 详情
(X) 23775 5-amino-2,3-dimethoxyphenol C8H11NO3 详情 详情
(XI) 23776 2,3-dimethoxy-5-[(9-methoxy-6,6-dimethyl-5,6-dihydrobenzo[h]quinazolin-2-yl)amino]phenol C23H25N3O4 详情 详情
(XII) 16194 2-chloro-N,N-diethyl-1-ethanamine; N-(2-chloroethyl)-N,N-diethylamine 100-35-6 C6H14ClN 详情 详情
Extended Information