1-(3', 4', 5'-tribasic-phenyl)-isoquinoline compound, its preparation and use
A compound, isoquinoline technology, applied in the field of medicinal chemistry and pharmacology, can solve the problems of limiting the general applicability of drugs, low selectivity, and unsatisfactory
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preparation example 1
[0143] Preparation Example 1: Preparation of Compound IV-1 [N-(3-benzyloxy)phenethyl-(3',5'-dimethoxy-4'-benzyloxy)benzamide]:
[0144]
[0145]Dissolve 4.4g (16.0mmol) of 3,5-methoxy-4-benzyloxy-benzoic acid in 200ml of dry dichloromethane, add 20ml (230mmol) of oxalyl chloride dropwise under ice-cooling conditions, and complete the reaction at room temperature After 2 hours, excess oxalyl chloride was distilled off under reduced pressure. The residue was redissolved in 50ml of dry dichloromethane, and added dropwise to a solution of 4.5g (19.8mmol) of 3-benzyloxyphenethylamine and 0.5ml of triethylamine in 200ml of dichloromethane under ice-cooling conditions After stirring at room temperature overnight, add 50ml of 10% sodium hydroxide solution, stir for 30 minutes, separate the organic phase, and wash with saturated sodium carbonate (50ml×2), water (50ml×2) and saturated saline (50ml×2) respectively. )washing. After drying over anhydrous magnesium sulfate and evaporat...
preparation example 2-13
[0149] Preparation Example 2-13: Prepare the compound of Preparation Example 2-13 shown in the following Table 1 according to the method of Preparation Example 1 above:
[0150]
[0151] Preparation example
No
compound
No
R 1
R 2
R 3
R 4
R 5
R 6
EIMS
2
IV-2
Oh
H
H
OCH 3
Oh
OCH 3
317(M) +
3
IV-3
H
OB
H
OCH 3
OB
OCH 3
497(M) +
4
IV-4
H
Oh
H
OCH 3
Oh
OCH 3
317(M) +
5
IV-5
H
OCH 3
H
OCH 3
OB
OCH 3
421(M) +
6
IV-6
H
OCH 3
H
OCH 3
Oh
OCH 3
331(M) +
7
IV-7
OCH 2 o
H
OCH 3
OB
OCH 3
435(M) +
8
IV-8
OCH 2 o
H
OCH 3
Oh
OCH 3
345(M) +
9...
preparation example 14
[0165] Preparation 14: Compound III-A1[6-benzyloxy-1-(3',5'-dimethoxy-4'-benzyloxyphenyl)-3,4-dihydroisoquinoline] preparation:
[0166]
[0167] Suspend 638 mg (1.28 mmol) of compound (IV-1) (see Preparation 1) in 50 ml of toluene, add 0.25 ml (2.6 mmol) of phosphorus oxychloride, reflux for 4 hours, cool to room temperature, and evaporate the toluene under reduced pressure , dissolve the residue in 30ml ethyl acetate, adjust the pH to 8-9 with concentrated ammonia water under ice-bath cooling, separate the water layer, extract with ethyl acetate (10ml×2), combine the organic phases, and successively water (10ml×2) 2), washed with saturated brine (10ml×2), dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether 1:2) to obtain 370 mg of solid with a yield of 60.3%.
[0168] III-A1 compound:
PUM
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