14756-77-5|1,5-Naphthyridin-3-amine| Ambeed

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Quality Control of [ 14756-77-5 ] Purity: 98% SDS Specification

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Product Details of [ 14756-77-5 ]

CAS No. :	14756-77-5
Formula :	C₈H₇N₃
M.W :	145.16
SMILES Code :	NC1=CC2=NC=CC=C2N=C1
MDL No. :	MFCD13189455
InChI Key :	QTNIZGZNNIWTGC-UHFFFAOYSA-N
Pubchem ID :	589351

Safety of [ 14756-77-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Application In Synthesis of [ 14756-77-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 14756-77-5 ]

[ 14756-77-5 ] Synthesis Path-Downstream 1~34

1
[ 74919-33-8 ]
[ 14756-77-5 ]

References: [1]Patent: DE700862,1938,C .
DRP/DRBP Org.Chem.,.
DRP/DRBP Org.Chem.,.

3
[ 67-56-1 ]
[ 74919-33-8 ]
palladium [ No CAS ]
[ 14756-77-5 ]

References: [1]Patent: DE700862,1938,C .
DRP/DRBP Org.Chem.,.
DRP/DRBP Org.Chem.,.

4
[ 64222-33-9 ]
[ 14756-77-5 ]

References: [1]Patent: DE700862,1938,C .
DRP/DRBP Org.Chem.,.
DRP/DRBP Org.Chem.,.

5
[ 959617-73-3 ]
[ 14756-77-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; In methanol; at 50℃; for 2h;	To a solution of tert-butyl l,5-naphthyridin-3-ylcarbamate (D-12) (4.040 g, 16.5 mmol, 1.0 eq) in methanol (24 mL), concentrated hydrochloric acid (36.5%, 10 mL, 120 mmol, 7.27 eq) was added. The resulting mixture was stirred at 50 C for 2 h. The reaction was complete based on TLC analysis. The mixture was concentrated under reduced pressure to afford the desired product l,5-naphthyridin-3-amine (D-13), which was used for next reaction without further purification. 'HNMR (300 MHz, DMSO-<¾) 8.85 (m, 1H), 8.77-8.75 (m, 2H),7.63-7.69(m, 1H), 7.4 (d, J= 1.8 Hz, 1H); ESI-MS m/z : 146.10 [M+H]+.
	With hydrogenchloride; In methanol; water; at 50℃; for 2h;	Example 2b: Synthesis of l,5-naphthyridin-3-amine [00316] To a solution of tert-butyl l,5-naphthyridin-3-ylcarbamate (D-12) (4.040 g, 16.5 mmol, 1.0 eq) in methanol (24 mL), concentrated hydrochloric acid (36.5%, 10 mL, 120 mmol, 7.27 eq) was added. The resulting mixture was stirred at 50 C for 2 h. The reaction was complete based on TLC analysis. The mixture was concentrated under reduced pressure to afford the desired product 1 ,5- naphthyridin-3 -amine (D-13), which was used for next reaction without further purification. 'HNMR (300 MHz, DMSO- 6) 8.85 (m, 1H), 8.77-8.75 (m, 2H),7.63-7.69(m, 1H), 7.4 (d, J = 1.8 Hz, 1H); ESI-MS m/z : 146.10 [M+H]+.
		To a solution of 1.00 g of tert-butyl 1,5-naphthyridin-3-ylcarbamate in 6 mL of methanol, 1 mL of a 12 mol/L aqueous hydrogen chloride solution was added, and the mixture was stirred for 30 minutes. To the reaction mixture, 5 mL of methanol and 1 mL of a 12 mol/L aqueous hydrogen chloride solution were added, and the mixture was stirred at 40C for 40 minutes, and at 80C for 40 minutes. In the reaction mixture, the solvent was distilled off under reduced pressure, the mixture was neutralized with a saturated aqueous sodium hydrogen carbonate solution, and then the solvent was distilled off under reduced pressure. The resultant residue was washed with ethanol and, in the mother liquid, the solvent was distilled off under reduced pressure, and the resultant residue was purified with silica gel column chromatography using silica gel; Chromatorex-NH made by Fuji Silysia Chemical Ltd., and an eluent of chloroform:methanol = 10:1 to obtain 0.50 g of 1,5-naphthyridin-3-amine as a yellow solid. 1H-NMR (CDCl3) δ: 4.18 (2H, s), 7.31-7.42 (1H, m), 7.43-7.50 (1H, m), 8.21-8.30 (1H, m), 8.51-8.62 (1H, m), 8.77-8.88 (1H, m)

References: [1]Patent: WO2011/149937,2011,A1 .Location in patent: Page/Page column 40; 80.
[2]Patent: WO2013/78441,2013,A1 .Location in patent: Paragraph 00143; 00316.
[3]Patent: WO2014/151147,2014,A1 .Location in patent: Paragraph 00641.
[4]Patent: US2015/30588,2015,A1 .Location in patent: Page/Page column 64; 65.
[5]Patent: US9295673,2016,B2 .Location in patent: Page/Page column 339; 340.
[6]Patent: EP2022793,2009,A1 .Location in patent: Page/Page column 106-107.

6
[ 14756-77-5 ]
[ 959617-74-4 ]

Yield	Reaction Conditions	Operation in experiment
		To 2 mL of hydrogen fluoride/pyridine, 145 mg of 1,5-naphthyridin-3-amine was added at 0C, 76 mg of sodium nitrite was added to the reaction mixture, and stirred at 0C for 1 hour. The reaction mixture was stirred at 60C for 1 hour, and neutralized with a saturated aqueous sodium hydrogen carbonate solution at 0C, chloroform was then added thereto, and the organic layer was separated. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using silica gel; Silica Gel 60N made by KANTO CHEMICAL CO., INC., and an eluent of chloroform:methanol = 20:1 to obtain 77 mg of 3-fluoro-1,5-naphthyridine as a light yellow solid. 1H-NMR (CDCl3) δ: 7.62-7.67 (1H, m), 8.03-8.08 (1H, m), 8.42-8.47 (1H, m), 8.90-8.94 (1H, m), 8.98-9.03 (1H, m)

References: [1]Patent: EP2022793,2009,A1 .Location in patent: Page/Page column 107.

7
[ 254-79-5 ]
[ 14756-77-5 ]

References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

8
[ 17965-71-8 ]
[ 14756-77-5 ]

References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .
[6]Patent: EP2022793,2009,A1 .

9
[ 14756-77-5 ]
[ 1228666-28-1 ]

Yield	Reaction Conditions	Operation in experiment
65.3%		Example 2c: Synthesis of 3-iodo-l,5-naphthyridine (D-14) [00317] To a solution of l,5-naphthyridin-3-amine (D-13) (16.5 mmol, 1.0 eq) in H20 (150 mL), con. HC1 (36.5%, 7 mL, 84 mmol, 5.0 eq) was added slowly at 0 - 5 C. The resulting mixture was stirred for 15 min at 0 - 5 C, a solution of sodium nitrite (1.252 g, 18.1 mmol, 1.1 eq) in H20 (5 mL) was added dropwise at 0 - 5 C and stirred for 1 h. Then the above solution was added to a solution of KI (8.217 g, 49.5 mmol, 3 eq) in H20 (100 mL), the resulting mixture was stirred at 60 C for 1 hour. After the solution was cooled to RT, solid Na2SC>3 (4.0 g) was added. The mixture was neutralized with solid Na2CC>3 to adjust pH value to 7 - 8, and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over Na2SC>4 and filtered. The filtrate was concentrated in vacuo to afford the desired product 3-iodo-l,5-naphthyridine (D-14) (2.758 g, 65.3% yield, 2 steps) as a solid. lR NMR (300 MHz, CDC13- 6) δ: 9.1 (d, J = 2.1 Hz, 1H), 8.95 (dd, J = 4.2 Hz, J = 1.5 Hz, 1H), 8.80 (d, J = 1.2 Hz, 1H), 8.35 (d, J = 8.4 Hz, 1H), 7.63-7.67(m, 1H); ESI-MS m/z : 256.96 [M+H]+.
		To a solution of l,5-naphthyridin-3-amine (D-13) (16.5 mmol, 1.0 eq) in H20 (150 mL), con. HC1 (36.5%, 7 mL, 84 mmol, 5.0 eq) was added slowly at 0 - 5 C. The resulting mixture was stirred for 15 min at 0 - 5 C, a solution of sodium nitrite (1.252 g, 18.1 mmol, 1.1 eq) in H20 (5 mL) was added dropwise at 0 - 5 C and stirred for 1 h. Then the above solution was added to a solution of KI (8.217 g, 49.5 mmol, 3 eq) in H20 (100 mL), the resulting mixture was stirred at 60 C for 1 hour. After the solution was cooled to RT, solid Na2S03 (4.0 g) was added. The mixture was neutralized with solid Na2C(¾ to adjust pH value to 7 - 8, and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to afford the desired product 3-iodo-l,5-naphthyridine (D-14) (2.758 g, 65.3%o yield, 2 steps) as a solid. :H NMR (300 MHz, CDC13-<¾) 8: 9.1 (d, J = 2.1 Hz, 1H), 8.95 (dd, J = 4.2 Hz, J = 1.5 Hz, 1H), 8.80 (d, J = 1.2 Hz, 1H), 8.35 (d, J= 8.4 Hz, 1H), 7.63-7.67(m, 1H); ESI-MS m/z : 256.96 [M+H]+.

References: [1]Patent: WO2013/78441,2013,A1 .Location in patent: Paragraph 00143; 00317.
[2]Patent: WO2011/149937,2011,A1 .Location in patent: Page/Page column 40; 80.
[3]Patent: WO2014/151147,2014,A1 .Location in patent: Paragraph 00641.
[4]Patent: US2015/30588,2015,A1 .Location in patent: Page/Page column 65.
[5]Patent: US9295673,2016,B2 .Location in patent: Page/Page column 339; 340.

10
[ 14756-77-5 ]
[ 1275607-94-7 ]

References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

11
[ 14756-77-5 ]
[ 1350925-13-1 ]

References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

12
[ 14756-77-5 ]
[ 1350925-14-2 ]

References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

13
[ 14756-77-5 ]
[ 1350925-15-3 ]

References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

14
[ 14756-77-5 ]
[ 1350925-16-4 ]

References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

15
[ 14756-77-5 ]
[ 1350925-17-5 ]

References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

16
[ 14756-77-5 ]
[ 1350925-18-6 ]

References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

17
[ 14756-77-5 ]
[ 1362739-44-3 ]

References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

18
[ 14756-77-5 ]
[ 959615-64-6 ]