Nitrogen-containing heterocylic compound or salt thereof
A nitrogen-heterocyclic compound and heterocyclic group technology, applied in organic chemistry, drug combination, medical preparations containing active ingredients, etc., can solve the problem of fewer compounds
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[0415] The present invention will be described with reference examples, examples, and test examples, but the present invention is not limited to these.
[0416] Unless otherwise stated, an automatic purification device ISOLERA (Biotage) or a medium pressure liquid chromatography YFLC W-prep2XY (Yamazen Co., Ltd.) is used for purification by column chromatography.
[0417] Unless otherwise stated, SNAP KP-Sil Cartridge (Biotage), HI-FLASH COLUMN W001, W002, W003, W004, or W005 (Shanzen Co., Ltd.) is used as a carrier in silica gel column chromatography.
[0418] SNAP KP-NH Cartridge (Biotage) was used for NH silica.
[0419] Preparation of thin-layer silica gel chromatography using PLC glass plate silica gel F 60 (Merck Corporation).
[0420] Initiator Sixty (Biotage) was used as the microwave reaction device.
[0421] H-Cube (Thales Nano Company) was used as the flow hydrogenation reactor.
[0422] The reverse phase preparative HPLC used Waters 2998 Photodiode Array (PDA) Detector (Waters...
Embodiment 0001
[0456]
[0457] [化13]
[0458]
[0459] Add triethylamine (13mL), butyl acrylate (10mL) and bis(tri-tert-butylphosphine) palladium (0) to 2-chloro-3-aminopyridine (6.00g) in cyclohexyl acetate (60mL) solution (350 mg), stirred for 40 hours at 150°C in a nitrogen atmosphere. Water (30 mL) was added to the reaction mixture at 70°C, and the mixture was cooled to room temperature while stirring. The reaction mixture was subjected to ultrasonic treatment for 30 minutes, and the solid matter was filtered and washed with water. Ethyl acetate (3 mL) / 2-propanol (4 mL) was added to the obtained solid, and ultrasonic treatment was performed. The solid matter was collected by filtration to obtain 1,5-naphthyridin-2-ol (2.51 g) as a pale yellow solid.
[0460] MSm / z(M+H): 147.
[0461]
[0462] [化14]
[0463]
[0464] Phosphorus oxychloride (8.3 mL) was added to 1,5-naphthyridin-2-ol (2.76 g), and the mixture was stirred at 100°C for 5 hours. The reaction mixture was cooled to room temperatur...
Embodiment 0002
[0483]
[0484] [化18]
[0485]
[0486] In Example 0001, 1-(3-morpholinylpropyl)-1H-pyrazole-4-boronic acid pinacol ester was used instead of 1-(2-morpholinylethyl)-1H-pyrazole- 4-(4-boronic acid pinacol ester), except that the same method as in Example 0001 was used to obtain 4-(2-(4-(6-chloro-1,5-naphthyridin-3-yl)-1H-pyrazole- 1-yl)ethyl)morpholine (96.9 mg).
[0487] MSm / z(M+H): 344.
[0488]
[0489] [化19]
[0490]
[0491] In Example 0001, 4-(3-(4-(6-chloro-1,5-naphthyridin-3-yl)-1H-pyrazol-1-yl)propyl) morpholine was used instead of 4- (2-(4-(6-chloro-1,5-naphthyridin-3-yl)-1H-pyrazol-1-yl)ethyl)morpholine, except that it was obtained in the same manner as in Example 0001 N-(7-(1-(2-morpholinylethyl)-1H-pyrazol-4-yl)-1,5-naphthyridin-2-yl)-1,3,4 as a pale yellow solid -Thiadiazole-2-amine (16.6 mg).
[0492] 1 H-NMR(DMSO-d 6 )δ: 12.24 (1H, s), 9.17 (1H, s), 9.09 (1H, d, J = 2.0 Hz), 8.57 (1H, s), 8.32 (1H, d, J = 2.0 Hz), 8.28 ( 1H, d, J = 8.9 Hz), 8.21 (1H, s), 7.44 (1H, d...
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