Alternatived Products of [ 114474-28-1 ]
Alternatived Products of [ 114474-28-1 ]
Product Details of [ 114474-28-1 ]
CAS No. : | 114474-28-1 | MDL No. : | MFCD11932600 |
Formula : |
C9H9N3
|
Boiling Point : |
- |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 159.19 | Pubchem ID : | 13977013 |
Synonyms : |
|
Computed Properties of [ 114474-28-1 ]
TPSA :Topological Polar Surface Area |
54.7 |
H-Bond Acceptor Count : |
2 |
XLogP3 : |
1.2 |
H-Bond Donor Count : |
2 |
SP3 : |
0.00 |
Rotatable Bond Count : |
1 |
Safety of [ 114474-28-1 ]
Application In Synthesis of [ 114474-28-1 ]
- Upstream synthesis route of [ 114474-28-1 ]
- Downstream synthetic route of [ 114474-28-1 ]
- 1
[ 114474-26-9 ]

[ 114474-28-1 ]
Yield | Reaction Conditions | Operation in experiment |
94% |
at 20℃; |
To a suspension of 4-(4-Nitrophenyl)-1H-pyrazole (8.3 g, 43.88 mmol) in MeOH/DME (2:1 v/v) was added 10percent Pd/C (wet, 415 mg). The reaction flask was purged with vacuum then filled with H2 from a balloon. This was done a total of 3 times. The reaction mixture was stirred at rt and checked by LC-MS for formation of the amine. After stirring for 2.5 at rt, LC-MS and tlc showed that there is a minor amount of SM in the reaction. An additional amount of catalyst (200 mg) was added to the reaction mixture and the reaction vessel was filled with H2 as before. The reaction was checked after 2h for disappearance of the remaining SM. At this time, the reaction was complete. The mixture was filtered on Celite and the Celite was washed with MeOH. The solvent was removed in vacuo to give 6.59 g (94percent) of a yellow solid. ‘H NIVIR (400 MHz, DMSO-d6) ö 12.68 (b, 1H), 7.80 (s, 2H), 7.23 (d, J = 8.0 Hz, 2H), 6.54 (d, J = 8.0 Hz, 2H), 4.97 (s, 2H). MS (ES+) m/e 160 (M+H)+. |
94% |
With palladium 10% on activated carbon; hydrogen In methanol; 1,2-dimethoxyethane at 20℃; for 2.00 h; |
[0092] To a suspension of 4-(4-Nitrophenyl)-lH-pyrazole (8.3 g, 43.88 mmol) in MeOH/DME (2: 1 v/v) was added 10percent Pd/C (wet, 415 mg). The reaction flask was purged with vacuum then filled with from a balloon. This was done a total of 3 times. The reaction mixture was stirred at rt and checked by LC-MS for formation of the amine. After stirring for 2.5 at rt, LC-MS and tic showed that there is a minor amount of SM in the reaction. An additional amount of catalyst (200 mg) was added to the reaction mixture and the reaction vessel was filled with as before. The reaction was checked after 2h for disappearance of the remaining SM. At this time, the reaction was complete. The mixture was filtered on Celite and the Celite was washed with MeOH. The solvent was removed in vacuo to give 6.59 g (94percent) of a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.68 (b, 1H), 7.80 (s, 2H), 7.23 (d, J = 8.0 Hz, 2H), 6.54 (d, J = 8.0 Hz, 2H), 4.97 (s, 2H). MS (ES+) m/e 160 (M+H)+. |
Reference:
[1] Patent: WO2016/210331, 2016, A1. Location in patent: Paragraph 0087; 0088
[2] Patent: WO2016/210330, 2016, A1. Location in patent: Paragraph 0091-0092
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 616 - 619
- 1
-
2-chloro-4-(1-ethyl-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidine
[ No CAS ]

-
[ 114474-28-1 ]

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N-(4-(1H-pyrazol-4-yl)phenyl)-4-(1-ethyl-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidin-2-amine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
61 mg |
In methanol; at 90.0℃; |
A mixture containing <strong>[114474-28-1]4-(1H-pyrazol-4-yl)aniline</strong> (77 mg), 2-chloro-4-(1-ethyl-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidine (Production Example 3, 115 mg)and methanol (0.5 mL) was stirred at 90 C. overnight. The reaction mixture was concentrated under a reduced pressure, the obtained residue was purified through silica gel column chromatography (elution solvent: dichloromethane-methanol), and thereby N-(4-(1H-pyrazol-4-yl)phenyl)-4-(1-ethyl-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidin-2-amine (61 mg)as a yellow solid was obtained. |
- 2
-
[ 4755-77-5 ]

-
[ 114474-28-1 ]

-
4-(1H-pyrazole-4-yl)phenylene-N-(ethyloxamate)
[ No CAS ]
- 3
-
[ 18915-53-2 ]

-
[ 114474-28-1 ]
- 4
-
2,4-dichloro-6-isopropoxyquinazoline
[ No CAS ]

-
[ 114474-28-1 ]

-
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-6-isopropoxyquinazolin-4-amine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
94% |
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃; |
To a solution of 2,4-dichloro-6-isopropoxyquinazoline (257 mg, 1.00 mmol) and 4-(4-aminophenyl)pyrazole amine (159 mg, 1.00 mmol) in DMF (2 mL) in a 1-dram vial was added DIEA (258 mg, 2.00 mmol, 0.348 mL). The mixture was heated at 100 C overnight. LC-MS showed one main peak corresponding to the desired product mass. The reaction mixture was cooled to rt and poured into water. The precipitate was filtered and washed with water. The resulting yellow solid was left to dry on the filter overnight to give the title compound (357 mg, 94%), as a yellow solid which was used as is in the next reaction. MS (ES+) m/e 380 (M+H)+. |
- 5
-
2,4-dichloro-6-(2-fluoroethoxy)quinazoline
[ No CAS ]

-
[ 114474-28-1 ]

-
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-6-(2-fluoroethoxy)quinazolin-4-amine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
71% |
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃; |
To a solution of 2,4-dichloro-6-(2-fluoroethoxy)quinazoline (201 mg, 0.77 mmol) and 4-(4-aminophenyl)pyrazole amine (122 mg, 0.77 mmol) in DMF (1.5 mL) in a 1- dram vial was added DIEA (199 mg, 1.54 mmol, 0.268 mL). The vial was flushed with nitrogen and the mixture was heated at 100 C overnight. LC-MS showed one main peak corresponding to the desired product mass. The reaction mixture was cooled to rt and poured into water. The precipitate was filtered and washed with water. The resulting yellow solid was left to dry on the filter for 3 h to give 210 mg, 71%, of a yellow solid which was used as is in the next reaction. MS (ES+) m/e 384 (M+H)+. |
- 6
-
2,4-dichloro-6-propoxyquinazoline
[ No CAS ]

-
[ 114474-28-1 ]

-
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-6-propoxyquinazolin-4-amine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃; |
To a solution of 2,4-dichloro-6-propoxyquinazoline (257 mg, 1.00 mmol) and 4-(4-aminophenyl)pyrazole amine (159 mg, 1.00 mmol) in DMF (2 mL) in a 1-dram vial was added DIEA (258 mg, 2.00 mmol, 0.348 mL). The mixture was heated at 100 C overnight. LC-MS showed one main peak corresponding to the desired product mass. The reaction mixture was cooled to rt and poured into water. The precipitate was filtered and washed with water. The resulting yellow solid was left to dry on the filter for 2 d to give 348 mg, 92%, of crude product which was used as is in the next reaction. MS (ES+) m/e 380/382 (M+H)+. |
- 7
-
2,4-dichloro-6-(2-methoxyethoxy)quinazoline
[ No CAS ]

-
[ 114474-28-1 ]

-
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-6-(2-methoxyethoxy)quinazolin-4-amine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100.0℃; |
To a solution of 2,4-dichloro-6-(2-methoxyethoxy)quinazoline (273 mg, 1.00 mmol) and 4-(4-aminophenyl)pyrazole amine (159 mg, 1.00 mmol) in DMF (2 mL) in a 1- dram vial was added DIEA (258 mg, 2.00 mmol, 0.348 mL). The mixture was heated at 100 C overnight. LC-MS showed one main peak corresponding to the desired product mass. The reaction mixture was cooled to rt and poured into water. The precipitate was filtered and washed with water. The resulting yellow solid was left to dry on the filter for 2 h to give 419 mg of crude product which was used as is in the next reaction. MS (ES+) m/e 396/398 (M+H)+. |
- 8
-
[ 174566-15-5 ]

-
[ 114474-28-1 ]

-
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-7-fluoroquinazolin-4-amine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
96% |
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 90℃; |
A mixture of 4-(lH-pyrazol-4-yl)aniline (120 mg, 0.75 mmol), 2,4-dichloro- 7-fluoroquinazoline (164 mg, 0.75 mmol), and zPrNEt2 (195 mg, 1.51 mmol) in DMF (2.51 mL) was stirred at 90 C overnight, cooled to rt, diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (245 mg, 96%). MS (ES+) m/e 340 (M+H)+. |
- 9
-
[ 134517-57-0 ]

-
[ 114474-28-1 ]

-
N-(4-(1H-pyrazol-4-yl)phenyl)-2-chloro-6-fluoroquinazolin-4-amine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
100% |
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 90.0℃; |
A mixture of 4-(lH-pyrazol-4-yl)aniline (120 mg, 0.75 mmol), 2,4-dichloro- 6-fluoroquinazoline (164 mg, 0.75 mmol), and z'Pr Et2 (195 mg, 1.51 mmol) in DMF (2.51 mL) was stirred at 90 C overnight, cooled to rt, diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (255 mg, 100%). MS (ES+) m/e 340 (M+H)+. |
- 10
-
[ 114474-28-1 ]

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2-(3-(4-((4-(1H-pyrazol-4-yl)phenyl)amino)-7-fluoroquinazolin-2-yl)phenoxy)-N-isopropylacetamide
[ No CAS ]