90008-50-7|6-Propoxypyridazin-3-amine| Ambeed

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Quality Control of [ 90008-50-7 ] Purity: 95+% SDS Specification

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Product Details of [ 90008-50-7 ]

CAS No. :	90008-50-7
Formula :	C₇H₁₁N₃O
M.W :	153.18
SMILES Code :	C(CC)OC1=CC=C(N=N1)N
MDL No. :	MFCD09835392
InChI Key :	YXEDABZQSZKQKZ-UHFFFAOYSA-N
Pubchem ID :	10511047

Safety of [ 90008-50-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 90008-50-7 ]

* 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 [ 90008-50-7 ]

[ 90008-50-7 ] Synthesis Path-Downstream 1~28

1
[ 71-23-8 ]
[ 5469-69-2 ]
[ 90008-50-7 ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4160 - 4163.

2
[ 40288-65-1 ]
[ 90008-50-7 ]
2-(3,4-methylenedioxyphenyl)-6-propoxy-imidazo[1,2-b]pyridazine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.

3
[ 70-11-1 ]
[ 90008-50-7 ]
[ 1844-70-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A stirred mixture of <strong>[90008-50-7]3-amino-6-propoxypyridazine</strong> 3 (4.50g, 29.4mmol), 2-bromo-1-[4-(2-methoxyethoxy)phenyl]ethanone 11 (8.03g, 29.4mmol) and EtOH (280mL) was heated at reflux for 2.5 hours. The mixture was cooled and NaHCO3 (2.50g, 30mmol) was added. The mixture was stirred at room temperature for 15 hours, heated at reflux for 1 hour, then cooled and evaporated. The residue was extracted with CHCl3 (150mL) and the extract washed with saturated, aqueous NaCl solution (50mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography over silica gel. Elution with 1-2% MeOH in CH2Cl2 afforded a green/brown solid. Treatment with decolourising charcoal and recrystallization from cyclohexane gave 6f (3.95g, 41%) as pale green crystals, m.p. 82.5-84C. 1H NMR (CDCl3) ? 1.06 (3H, t, J=7.2Hz), 1.75-1.94 (2H, m), 3.47 (3H, s), 3.74-3.81 (2H, m), 4.14-4.21 (2H, m), 4.27 (2H, t, J=6.6Hz), 6.68 (1H, d, J=9.3Hz), 7.00 (2H, d, J=8.8Hz), 7.76-7.88 (3H, m), 7.94 (1H, s). MS (APCI+) m/z 328 (M+H, 100%).

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4160 - 4163.

4
[ 619-41-0 ]
[ 90008-50-7 ]
[ 184015-01-8 ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.

5
[ 536-38-9 ]
[ 90008-50-7 ]
[ 3748-69-4 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A stirred mixture of <strong>[90008-50-7]3-amino-6-propoxypyridazine</strong> 3 (4.50g, 29.4mmol), 2-bromo-1-[4-(2-methoxyethoxy)phenyl]ethanone 11 (8.03g, 29.4mmol) and EtOH (280mL) was heated at reflux for 2.5 hours. The mixture was cooled and NaHCO3 (2.50g, 30mmol) was added. The mixture was stirred at room temperature for 15 hours, heated at reflux for 1 hour, then cooled and evaporated. The residue was extracted with CHCl3 (150mL) and the extract washed with saturated, aqueous NaCl solution (50mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography over silica gel. Elution with 1-2% MeOH in CH2Cl2 afforded a green/brown solid. Treatment with decolourising charcoal and recrystallization from cyclohexane gave 6f (3.95g, 41%) as pale green crystals, m.p. 82.5-84C. 1H NMR (CDCl3) ? 1.06 (3H, t, J=7.2Hz), 1.75-1.94 (2H, m), 3.47 (3H, s), 3.74-3.81 (2H, m), 4.14-4.21 (2H, m), 4.27 (2H, t, J=6.6Hz), 6.68 (1H, d, J=9.3Hz), 7.00 (2H, d, J=8.8Hz), 7.76-7.88 (3H, m), 7.94 (1H, s). MS (APCI+) m/z 328 (M+H, 100%).

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4160 - 4163.

7
[ 5469-69-2 ]
[ 6819-41-6 ]
[ 90008-50-7 ]

References: [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 1215 - 1218.

8
[ 28621-53-6 ]
[ 90008-50-7 ]
4-dimethylamino-2,2-dioxo-7-propoxy-2H-2λ⁶-pyridazo[3,2-c][1,2,4,6]thiatriazine [ No CAS ]

References: [1]Australian Journal of Chemistry,2007,vol. 60,p. 105 - 112.

9
[ 90008-50-7 ]
N-(2-Phenyl-6-propoxy-imidazo[1,2-b]pyridazin-3-ylmethyl)-benzamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.

10
[ 90008-50-7 ]
N-(6-Propoxy-2-p-tolyl-imidazo[1,2-b]pyridazin-3-ylmethyl)-benzamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.

11
[ 90008-50-7 ]
N-[2-(4-Chloro-phenyl)-6-propoxy-imidazo[1,2-b]pyridazin-3-ylmethyl]-benzamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.

12
[ 90008-50-7 ]
2-Fluoro-N-(6-propoxy-2-p-tolyl-imidazo[1,2-b]pyridazin-3-ylmethyl)-benzamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.

13
[ 90008-50-7 ]
2-Fluoro-N-(2-phenyl-6-propoxy-imidazo[1,2-b]pyridazin-3-ylmethyl)-benzamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.

14
[ 90008-50-7 ]
N-(2-Benzo[1,3]dioxol-5-yl-6-propoxy-imidazo[1,2-b]pyridazin-3-ylmethyl)-benzamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 651 - 662.

15
[ 79406-85-2 ]
[ 90008-50-7 ]
[ 860019-36-9 ]

Yield	Reaction Conditions	Operation in experiment
41%		A stirred mixture of <strong>[90008-50-7]6-propoxypyridazin-3-amine</strong> (4. 50g, 29. 4mmol), 2-bromo- 1- [4- (2-methoxyethoxy) phenyl] ethanone (8.03g, 29. 4mmol) and ethanol (280mL) was heated under reflux for 2.5 hours. The mixture was cooled and sodium bicarbonate (2. 50g, 30mmol) added. The mixture was stirred at room temperature for 15 hours, heated under reflux for 1 hour, then cooled and evaporated. The residue was extracted with chloroform (150mL) and the extract washed with saturated, aqueous, sodium chloride solution (50mL), dried (MgS04) and evaporated. The residue was purified by flash chromatography on silica gel. Elution with 1-2% methanol in dichloromethane afforded a green/brown solid. Treatment with decolourising charcoal in diethyl ether solution (three times) and recrystallization from cyclohexane gave Compound 63 (3.95g, 41%) as pale green crystals. M. p. 82. 5-84C.'H n. m. r. (CDC13) 8 1.06, t, J=7.2Hz, 3H; 1.75-1. 94, m, 2H; 3.47, s, 3H; 3.74-3. 81, m, 2H; 4. 14-4. 21, m, 2H; 4.27, t, J=6. 6Hz, 2H; 6. 68, d, J=9. 3Hz, 1H; 7.00, d, J=8.8Hz, 2H; 7.76-7. 88, m, 3H; 7.94, s, 1H. Mass spectrum (APCI+) m/z 328 (M+H, 100%).
41%		General procedure: A stirred mixture of <strong>[90008-50-7]3-amino-6-propoxypyridazine</strong> 3 (4.50g, 29.4mmol), 2-bromo-1-[4-(2-methoxyethoxy)phenyl]ethanone 11 (8.03g, 29.4mmol) and EtOH (280mL) was heated at reflux for 2.5 hours. The mixture was cooled and NaHCO3 (2.50g, 30mmol) was added. The mixture was stirred at room temperature for 15 hours, heated at reflux for 1 hour, then cooled and evaporated. The residue was extracted with CHCl3 (150mL) and the extract washed with saturated, aqueous NaCl solution (50mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography over silica gel. Elution with 1-2% MeOH in CH2Cl2 afforded a green/brown solid. Treatment with decolourising charcoal and recrystallization from cyclohexane gave 6f (3.95g, 41%) as pale green crystals, m.p. 82.5-84C. 1H NMR (CDCl3) ? 1.06 (3H, t, J=7.2Hz), 1.75-1.94 (2H, m), 3.47 (3H, s), 3.74-3.81 (2H, m), 4.14-4.21 (2H, m), 4.27 (2H, t, J=6.6Hz), 6.68 (1H, d, J=9.3Hz), 7.00 (2H, d, J=8.8Hz), 7.76-7.88 (3H, m), 7.94 (1H, s). MS (APCI+) m/z 328 (M+H, 100%).

References: [1]Patent: WO2005/66177,2005,A1 .Location in patent: Page/Page column 21-22.
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4160 - 4163.

16
[ 20933-24-8 ]
[ 90008-50-7 ]
3-methoxy-8-propoxy-5,6-dihydro-6b,7,11-triaza-benzo[a]fluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A stirred mixture of <strong>[90008-50-7]6-propoxypyridazin-3-amine</strong> (120mg, 0.78mmol), 2- bromo-6-methoxy-3, 4-dihydronaphthalen-1 (2H)-one (200mg, 0.78mmol) in ethanol was heated under reflux for 0.5 hours. The mixture was cooled and sodium bicarbonate (66mg, 0. 78mmol) added. The mixture was stirred at room temperature for 3 days and evaporated. The residue was extracted with chloroform and the extract washed with saturated, aqueous, sodium chloride solution, dried (MgS04) and evaporated. The residue was purified by flash chromatography on silica gel. Elution with 1-2% methanol in dichloromethane afforded Compound 121 (30mg) as a white solid n. m. r. (CDC13) 8 1.05, t, J=7.4Hz, 3H; 1.74-1. 94, m, 2H; 3.14, s, 4H; 3.82, s, 3H; 4. 28, t, J=6. 8Hz, 2H; 6.60, d, J=9.9Hz, 1H ; 6.78-6. 89, m, 2H; 7.77, d, J=9.6Hz, 1H ; 7.87, d, J=7.9Hz, 1H.

References: [1]Patent: WO2005/66177,2005,A1 .Location in patent: Page/Page column 30.

17
[ 90008-50-7 ]
[ 1775-27-5 ]
3-propoxy-5H-4,4a,10-triaza-indeno[2,1-a]indene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A stirred mixture of <strong>[90008-50-7]6-propoxypyridazin-3-amine</strong> (145mg) and 2-bromo-1-indanone (200mg) in ethanol (lOmL) was heated under reflux for 3 hours. The mixture was cooled and sodium bicarbonate (80mg) was added. The mixture was stirred refluxed for 1 hour and then the ethanol was evaporated. The residue was extracted with chloroform and the extract washed with saturated, aqueous, sodium chloride solution, dried (MgS04) and evaporated. The residue was purified by flash chromatography on silica gel. Elution with 1-2% methanol in dichloromethane afforded Compound 123 (30mg) as a white solid n. m. r. (CDC13) S 1.12, t, 3H; 1. 87, sextet, 2H; 3.85, s, 2H; 4.30, t, 2H; 6.64, d, 1H; 7.30, d, 1H ; 7.40, t, 1H; 7.53, d, 1H; 7.80-7. 88, m, 2H.

References: [1]Patent: WO2005/66177,2005,A1 .Location in patent: Page/Page column 30.

18
2-bromo-1-(4-(2-ethoxyethoxy)phenyl)ethan-1-one [ No CAS ]
[ 90008-50-7 ]
C₁₉H₂₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A stirred mixture of <strong>[90008-50-7]3-amino-6-propoxypyridazine</strong> 3 (4.50g, 29.4mmol), 2-bromo-1-[4-(2-methoxyethoxy)phenyl]ethanone 11 (8.03g, 29.4mmol) and EtOH (280mL) was heated at reflux for 2.5 hours. The mixture was cooled and NaHCO3 (2.50g, 30mmol) was added. The mixture was stirred at room temperature for 15 hours, heated at reflux for 1 hour, then cooled and evaporated. The residue was extracted with CHCl3 (150mL) and the extract washed with saturated, aqueous NaCl solution (50mL), dried (MgSO4) and evaporated. The residue was purified by flash chromatography over silica gel. Elution with 1-2% MeOH in CH2Cl2 afforded a green/brown solid. Treatment with decolourising charcoal and recrystallization from cyclohexane gave 6f (3.95g, 41%) as pale green crystals, m.p. 82.5-84C. 1H NMR (CDCl3) ? 1.06 (3H, t, J=7.2Hz), 1.75-1.94 (2H, m), 3.47 (3H, s), 3.74-3.81 (2H, m), 4.14-4.21 (2H, m), 4.27 (2H, t, J=6.6Hz), 6.68 (1H, d, J=9.3Hz), 7.00 (2H, d, J=8.8Hz), 7.76-7.88 (3H, m), 7.94 (1H, s). MS (APCI+) m/z 328 (M+H, 100%).