[ CAS No. 56621-89-7 ] {[proInfo.proName]}

Name: 56621-89-7|5-Amino-2-methoxypyrimidine|98%
Brand: Ambeed
SKU: A136098
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Quality Control of [ 56621-89-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 56621-89-7 ]

Product Details of [ 56621-89-7 ]

CAS No. :	56621-89-7	MDL No. :	MFCD08234878
Formula :	C₅H₇N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HKHRENFWPKWVML-UHFFFAOYSA-N
M.W :	125.13	Pubchem ID :	352904
Synonyms :

Calculated chemistry of [ 56621-89-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	32.93
TPSA :	61.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.14
Log Po/w (XLOGP3) :	-0.17
Log Po/w (WLOGP) :	0.08
Log Po/w (MLOGP) :	-0.9
Log Po/w (SILICOS-IT) :	0.2
Consensus Log Po/w :	0.07

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.94
Solubility :	14.5 mg/ml ; 0.116 mol/l
Class :	Very soluble
Log S (Ali) :	-0.66
Solubility :	27.6 mg/ml ; 0.221 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.38
Solubility :	5.24 mg/ml ; 0.0419 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.89

Safety of [ 56621-89-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 56621-89-7 ]

* 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.

Upstream synthesis route of [ 56621-89-7 ]
Downstream synthetic route of [ 56621-89-7 ]

[ 56621-89-7 ] Synthesis Path-Upstream 1~1

1
[ 14001-69-5 ]
[ 56621-89-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In methanol at 20℃; for 18 h;	Example 40Synthesis of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.To a solution of sodium methoxide (0.090 g of sodium) in MeOH (12 mL) was added 0.486 g (3.03 mmol) of 2-chloro-5-nitropyrimidine, and the mixture was heated under reflux for 1 hr. After cooling, the mixture was concentrated in vacuo, extracted with EtOAc, and washed with water. The aqueous layer was extracted with CHCl₃and the combined organic layers were dried (Na₂SO₄), and concentrated, to give 0.347 g (75percent yield) of 2-methoxy-5-nitropyrimidine as a yellow powder: ¹H NMR (CDCl₃) δ9.31 (s, 2H), 4.17 (s, 3H); LCMS (APCI⁺) m/z: 156 (MH⁺, 100percent).To 0.342 g (2.20 mmol) of the above nitro compound in MeOH (20 mL) was added 0.30 g of 10percent Pd/C and the mixture was stirred under hydrogen (25 in/Hg) for 18 hrs. The reaction mixture was filtered through celite, and concentrated, to give 0.274 g (100percent yield) of 5-amino-2-methoxypyrimidine as a colorless oil: ¹H NMR (DMSO-d₆) δ 8.05 (s, 2H), 3.94 (s, 3H); LCMS (APCI⁺) m/z: 126 (MH⁺, 100percent).To 0.274 g (2.19 mmol) of the above amino compound in THF (3 mL) was added 1.25 mL of NaHMDS (2 M solution in THF) and the mixture was stirred for 10 min. A solution of 0.31 g (0.78 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole in THF (5 mL) was added and the resulting mixture was stirred for 90 min. The reaction mixture was neutralized with acetic acid, diluted with water, and extracted with EtOAc. The organic layer was washed with water and aq. NH₃, dried, and concentrated. Recrystallization from EtOH/CH₂Cl₂gave 0.098 g (26percent yield) of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 255-258° C.; ¹H NMR (DMSO-d₆) 810.07 (s, 1H), 8.88-8.74 (m, 2H), 8.15-7.42 (m, 3H), 6.97 (d, J=8.0 Hz, 1H), 3.98 (s, 3H), 3.93 (s, 3H), 3.82-3.72 (m, 8H); Anal. Calcd. for C₂₁H₂₁F₂N₆O₃: C, 52.0; H, 4.4; N, 26.0. Found: C, 52.1; H, 4.5; N, 26.0percent.

Reference： [1] Patent: US2011/9405, 2011, A1, . Location in patent: Page/Page column 55-56

[ 56621-89-7 ] Synthesis Path-Downstream 1~48

1
[ 50-84-0 ]
[ 56621-89-7 ]
2-chloro-4-(2-methoxy-pyrimidin-5-ylamino)-benzoic acid [ No CAS ]

Reference： [1]Journal of the Chemical Society,1957,p. 4997,5000

2
[ 56621-89-7 ]
[ 98-74-8 ]
[ 71119-37-4 ]

Reference： [1]Patent: US2430439,1940,

3
[ 56621-89-7 ]
[ 121-60-8 ]
[ 71119-37-4 ]

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 567,569,570

4
[ 10031-82-0 ]
[ 56621-89-7 ]
[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-(2-methoxy-pyrimidin-5-yl)-amine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 1201 - 1208
Khimiya Geterotsiklicheskikh Soedinenii,1982,vol. 18,p. 1545 - 1552

5
[ 123-11-5 ]
[ 56621-89-7 ]
[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-(2-methoxy-pyrimidin-5-yl)-amine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 1201 - 1208
Khimiya Geterotsiklicheskikh Soedinenii,1982,vol. 18,p. 1545 - 1552

6
[ 5736-94-7 ]
[ 56621-89-7 ]
[1-(4-Hexyloxy-phenyl)-meth-(E)-ylidene]-(2-methoxy-pyrimidin-5-yl)-amine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 1201 - 1208
Khimiya Geterotsiklicheskikh Soedinenii,1982,vol. 18,p. 1545 - 1552

7
[ 50262-46-9 ]
[ 56621-89-7 ]
(2-Methoxy-pyrimidin-5-yl)-[1-(4-nonyloxy-phenyl)-meth-(E)-ylidene]-amine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 1201 - 1208
Khimiya Geterotsiklicheskikh Soedinenii,1982,vol. 18,p. 1545 - 1552

8
[ 56621-89-7 ]
[ 5736-91-4 ]
[1-(4-Butoxy-phenyl)-meth-(E)-ylidene]-(2-methoxy-pyrimidin-5-yl)-amine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 1201 - 1208
Khimiya Geterotsiklicheskikh Soedinenii,1982,vol. 18,p. 1545 - 1552

Yield	Reaction Conditions	Operation in experiment
	With copper; In methanol; at 150℃; for 24h;Sealed tube;	General procedure: To a solution of 5-chloropyrazin-2-amine (0.2 g, 1.54 mmol) in MeOH (3 mL) was added Cu powder (0.13 g, 2.07 mmol), followed by a solution of sodium methoxide in MeOH (0.38 mL, 1.75 mmol). The reaction mixture was stirred at 150C in a sealed tube for 24 h. The reaction mixture was then filtered through Celite, and the filtrate was concentrated in vacuo. The crude product obtained was purified by column chromatography (silica: 100-200 mesh, MeOH:DCM 2-3%) to afford the title compound (0.13 g, 67%). LCMS (ES+) 126 (M+H)+, RT 1.06 minutes (method 1).
	With copper; In methanol; at 150℃; for 24h;Sealed tube;	General procedure: Intermediate 22 5-Methoxypyrazin-2-amine [0242] To a solution of 5-chloropyrazin-2-amine (0.2 g, 1.54 mmol) in MeOH (3 mL) was added Cu powder (0.13 g, 2.07 mmol), followed by a solution of sodium methoxide in MeOH (0.38 mL, 1.75 mmol). The reaction mixture was stirred at 150 C. in a sealed tube for 24 h. The reaction mixture was then filtered through Celite, and the filtrate was concentrated in vacuo. The crude product obtained was purified by column chromatography (silica: 100-200 mesh, MeOH: DCM 2-3%) to afford the title compound (0.13 g, 67%). LCMS (ES+) 126 (M+H)+, RT 1.06 minutes (method 1).

10
[ 14001-69-5 ]
[ 56621-89-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 635.0 Torr; for 18h;	Example 40Synthesis of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.To a solution of sodium methoxide (0.090 g of sodium) in MeOH (12 mL) was added 0.486 g (3.03 mmol) of 2-chloro-5-nitropyrimidine, and the mixture was heated under reflux for 1 hr. After cooling, the mixture was concentrated in vacuo, extracted with EtOAc, and washed with water. The aqueous layer was extracted with CHCl3 and the combined organic layers were dried (Na2SO4), and concentrated, to give 0.347 g (75% yield) of 2-methoxy-5-nitropyrimidine as a yellow powder: 1H NMR (CDCl3) delta9.31 (s, 2H), 4.17 (s, 3H); LCMS (APCI+) m/z: 156 (MH+, 100%).To 0.342 g (2.20 mmol) of the above nitro compound in MeOH (20 mL) was added 0.30 g of 10% Pd/C and the mixture was stirred under hydrogen (25 in/Hg) for 18 hrs. The reaction mixture was filtered through celite, and concentrated, to give 0.274 g (100% yield) of 5-amino-2-methoxypyrimidine as a colorless oil: 1H NMR (DMSO-d6) delta 8.05 (s, 2H), 3.94 (s, 3H); LCMS (APCI+) m/z: 126 (MH+, 100%).To 0.274 g (2.19 mmol) of the above amino compound in THF (3 mL) was added 1.25 mL of NaHMDS (2 M solution in THF) and the mixture was stirred for 10 min. A solution of 0.31 g (0.78 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole in THF (5 mL) was added and the resulting mixture was stirred for 90 min. The reaction mixture was neutralized with acetic acid, diluted with water, and extracted with EtOAc. The organic layer was washed with water and aq. NH3, dried, and concentrated. Recrystallization from EtOH/CH2Cl2 gave 0.098 g (26% yield) of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 255-258 C.; 1H NMR (DMSO-d6) 810.07 (s, 1H), 8.88-8.74 (m, 2H), 8.15-7.42 (m, 3H), 6.97 (d, J=8.0 Hz, 1H), 3.98 (s, 3H), 3.93 (s, 3H), 3.82-3.72 (m, 8H); Anal. Calcd. for C21H21F2N6O3: C, 52.0; H, 4.4; N, 26.0. Found: C, 52.1; H, 4.5; N, 26.0%.

Reference： [1]Patent: US2011/9405,2011,A1 .Location in patent: Page/Page column 55-56

11
[ 1379860-81-7 ]
[ 56621-89-7 ]
[ 1253574-90-1 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7796 - 7816

12
[ 56621-89-7 ]
[ 1253574-91-2 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7796 - 7816

13
[ 56621-89-7 ]
[ 1253574-92-3 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7796 - 7816

14
[ 56621-89-7 ]
C₃₅H₄₀N₁₀O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7796 - 7816

15
[ 70-34-8 ]
[ 56621-89-7 ]
[ 1420044-40-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 744 - 749

16
[ 56621-89-7 ]
[ 1420044-52-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 744 - 749

17
[ 56621-89-7 ]
[ 1420044-65-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 744 - 749

18
[ 56621-89-7 ]
C₁₄H₁₅N₅O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 744 - 749

19
2-chloro-4-[(2S,5R)-2,5-dimethylpiperazin-1-yl]benzonitrile [ No CAS ]
[ 1885-14-9 ]
[ 56621-89-7 ]
[ 1372927-80-4 ]

Yield	Reaction Conditions	Operation in experiment
81%		General procedure: To a mixture of <strong>[56621-89-7]2-methoxypyrimidine-5-amine</strong> (120 mg) and pyridine (4 ml) was added phenyl chlorocarbonate (0.132 ml) under ice bath cooling, followed by stirring at room temperature for 1.5 hours. Thereafter, a mixture of 2-chloro-4-[(2S,5R)-2,5-dimethylpiperazin-1-yl]benzonitrile (200 mg) and pyridine (3 ml) was added thereto, followed by stirring at 100 C. for 1 hour. After cooling, the reaction solution was concentrated under reduced pressure, and toluene (15 ml×2) was added to the residue and the azeotrope was evaporated. Ethyl acetate (20 ml) was added to the residue, followed by washing with a saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over anhydrous sodium sulfate. Then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 96/4), to afford 258 mg (81%) of (2R,5S)-4-(3-chloro-4-cyanophenyl)-N-(2-methoxypyrimidin-5-yl)-2,5-dimethylpiperazine-1-carboxamide

Reference： [1]Patent: US2013/197009,2013,A1 .Location in patent: Paragraph 0152

20
2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]acetic acid [ No CAS ]
[ 56621-89-7 ]
2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]-N-(2-methoxypyrimidin-5-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		Example 82 Preparation of 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]-N-(2-methoxypyrimidin-5-yl)acetamide. TBTU (244 mg; 0.74 mmol; 1.5 eq) and DIPEA (170 muL; 0.99 mmol; 2 eq) were added to a solution of 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]acetic acid (1-21) (200 mg; 0.50 mmol; 1 eq) in anhydrous dioxane (8 mL). The reaction mixture was stirred at room temperature for 30 minutes. 2-Methoxypyrimidin-5-amine (124 mg; 0.99 mmol; 2 eq) was added and the reaction mixture was stirred at room temperature for 18 hours. Saturated ammonium chloride (20 mL) was added and the aqueous layer was extracted with ethyl acetate (2 x 30 mL). The combined organic layers were washed with saturated sodium chloride (1 x 20 mL), filtered and evaporated to dryness. The crude was purified on silica gel using dichloromethane/methanol (98/2) as an eluent. After trituration in diethyl ether, the title compound 2-[1-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2-sulfanylidene imidazolidin-4-yl]-N-(2-methoxypyrimidin-5-yl)acetamide was obtained in 25 % yield (79 mg) as a white solid. 1H-NMR (Acetone-d6): delta (ppm) delta 2.96 (m, 1H), 3.09 (m, 1H), 3.24 (m, 1H), 3.43 (m, 1H), 3.75 (s, 3H), 3.78 (m, 1H), 3.92 (s, 3H), 4.30 (m, 1H), 4.65 (s, 1H), 6.86 (m, 2H), 7.25 (m, 4H), 7.45 (m, 2H), 8.75 (m, 2H) 9.62 (m, 1H); MS (ESI+): m/z = 509.9 [M+H]+.
25%		Example 82: Preparation of2-[l-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5- oxo-2-mlfanylideneimid zolidin-4-yl]-N-{2-methoxypyrim TBTU (244 mg; 0.74 mmol; 1.5 eq) and DIPEA (170 mu 0.99 mmol; 2 eq) were added to a solution of 2-[l-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5-oxo-2- sulfanylideneimidazolidin-4-yl]acetic acid (1-21) (200 mg; 0.50 mmol; 1 eq) in anhydrous dioxane (8 mL). The reaction mixture was stirred at room temperature for 30 minutes. 2-Methoxypyrimidin-5-amine (124 mg; 0.99 mmol; 2 eq) was added and the reaction mixture was stirred at room temperature for 18 hours. Saturated ammonium chloride (20 mL) was added and the aqueous layer was extracted with ethyl acetate (2 x 30 mL). The combined organic layers were washed with saturated sodium chloride (1 x 20 mL), filtered and evaporated to dryness. The crude was purified on silica gel using dichloromethane/methanol (98/2) as an eluent. After trituration in diethyl ether, the title compound 2-[l-(4-fluorophenyl)-3-[2-(4- methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]-N-(2- methoxypyrimidin-5-yl)acetamide was obtained in 25% yield (79 mg) as a white solid. 1H-NMR (Acetone-d6): delta (ppm) delta 2.96 (m, 1H), 3.09 (m, 1H), 3.24 (m, 1H), 3.43 (m, 1H), 3.75 (s, 3H), 3.78 (m, 1H), 3.92 (s, 3H), 4.30 (m, 1H), 4.65 (s, 1H), 6.86 (m, 2H), 7.25 (m, 4H), 7.45 (m, 2H), 8.75 (m, 2H) 9.62 (m, 1H); MS (ESI+): m/z = 509.9 [M+H]+ .

Reference： [1]Patent: EP2664616,2013,A1 .Location in patent: Paragraph 0202-0203
[2]Patent: WO2013/171281,2013,A1 .Location in patent: Page/Page column 106-107

21
2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-1-(4-fluorophenyl)-5-oxo-2-sulfanylideneimidazolidin-4-yl)acetic acid [ No CAS ]
[ 56621-89-7 ]
2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-1-(4-fluorophenyl)-5-oxo-2-sulfanylideneimidazolidin-4-yl)-N-(2-methoxypyrimidin-5-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%		Example 79 Preparation of 2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-1-(4-fluorophenyl)-5-oxo-2-sulfanylideneimidazolidin-4-yl)-N-(2-methoxypyrimidin-5-yl)acetamide. TBTU (177.2 mg; 0.54 mmol; 1.5 eq) and DIPEA (126 muL; 0.72 mmol; 2 eq) were added to a solution of 2-(3- {2-[4-(dimethylamino)phenyl]ethyl}-1-(4-fluorophenyl)-5-oxo-2-sulfanylideneimidazolidin-4-yl)acetic acid (1-37) (150 mg; 0.36 mmol; 1 eq) in dioxane (6 mL). The reaction mixture was stirred at room temperature for 30 minutes. A solution of <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong> (90.3 mg; 0.72 mmol; 2 eq) in dimethylformamide (2 mL) was added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated to dryness. Saturated ammonium chloride was added (15 mL) and the aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with saturated sodium chloride (3 x 20 mL), dried over sodium sulfate and concentrated to dryness. The crude was purified by flash chromatography on silica gel using cyclohexane/ethyl acetate (25/75 to 0/100) as an eluent. After trituration in diethyl ether/dichloromethane, the title compound 2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-1-(4-fluorophenyl)-5-oxo-2-sulfanylidene imidazolidin-4-yl)-N-(2-methoxypyrimidin-5-yl)acetamide was obtained in 28 % yield (52 mg) as an off-white solid. 1H-NMR (DMSO-d6): delta (ppm) 2.75 (m, 1H), 2.84 (s, 6H), 2.94 (m, 1H), 3.15 (d, 1H), 3.28 (m, 1H), 3.64 (m, 1H), 3.89 (s, 3H), 4.13 (m, 1H), 4.73 (m, 1H), 6.65 (d, 2H), 7.07 (d, 2H), 7.37 (m, 4H), 8.72 (d, 2H), 10.5 (s, 1H); MS (ESI+): m/z = 522.9 [M+H]+.
28%		Example 79: Preparation of 2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-l-(4- fluorophenyl)-5-oxo-2-sulfanylideneimidazolidin-4-yl)-N-(2-methoxypyrim yl)acetamide. TBTU (177.2 mg; 0.54 mmol; 1.5 eq) and DIPEA (126 mu 0.72 mmol; 2 eq) were added to a solution of 2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-l-(4-fluorophenyl)- 5-oxo-2-sulfanylideneimidazolidin-4-yl)acetic acid (1-37) (150 mg; 0.36 mmol; 1 eq) in dioxane (6 mL). The reaction mixture was stirred at room temperature for 30 minutes. A solution of <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong> (90.3 mg; 0.72 mmol; 2 eq) in dimethylformamide (2 mL) was added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated to dryness. Saturated ammonium chloride was added (15 mL) and the aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with saturated sodium chloride (3 x 20 mL), dried over sodium sulfate and concentrated to dryness. The crude was purified by flash chromatography on silica gel using cyclohexane/ethyl acetate (25/75 to 0/100) as an eluent. After trituration in diethyl ether/dichloromethane, the title compound 2-(3-{2-[4-(dimethylamino) phenyl]ethyl}-l-(4-fluorophenyl)-5-oxo-2-sulfanylideneimidazolidin-4-yl)-N-(2- methoxypyrimidin-5-yl)acetamide was obtained in 28% yield (52 mg) as an off- white solid. 1H-NMR (DMSO-d6): delta (ppm) 2.75 (m, IH), 2.84 (s, 6H), 2.94 (m, IH), 3.15 (d, IH), 3.28 (m, IH), 3.64 (m, IH), 3.89 (s, 3H), 4.13 (m, IH), 4.73 (m, IH), 6.65 (d, 2H), 7.07 (d, 2H), 7.37 (m, 4H), 8.72 (d, 2H), 10.5 (s, IH); MS (ESI+): m/z = 522.9 [M+H]+ .

Reference： [1]Patent: EP2664616,2013,A1 .Location in patent: Paragraph 0251-0252
[2]Patent: WO2013/171281,2013,A1 .Location in patent: Page/Page column 129-130

22
2-[1-(4-fluorophenyl)-2,5-dioxo-3-[2-(thiophen-2-yl)ethyl]imidazolidin-4-yl]acetic acid [ No CAS ]
[ 56621-89-7 ]
2-[1-(4-fluorophenyl)-2,5-dioxo-3-[2-(thiophen-2-yl)ethyl]imidazolidin-4-yl]-N-(2-methoxypyrimidin-5-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide; at 20℃;	Example 80 Preparation of 2-[1-(4-fluorophenyl)-2,5-dioxo-3-[2-(thiophen-2-yl)ethyl]imidazolidin-4-yl]-N-(2-methoxypyrimidin-5-yl)acetamide. TBTU (265.8 mg; 0.83 mmol; 1.5 eq), followed by DIPEA (288 muL; 1.66 mmol; 3 eq) and after 10 minutes, <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong> (103.6 mg; 0.83 mmol; 1.5 eq) were added to a solution of 2-[1-(4-fluorophenyl)-2,5-dioxo-3-[2-(thiophen-2-yl)ethyl] imidazolidin-4-yl] acetic acid (1-17) (200 mg; 0.55 mmol; 1 eq) in dioxane/dimethylformamide (3 mL/300 muL). The reaction mixture was stirred at room temperature overnight. Saturated sodium hydrogenocarbonate (15 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with saturated sodium chloride (3 x 5 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel using dichloromethane/methanol (100/0 to 97/3) as an eluent. After washing in hydrochloric acid 1M and trituration in diethyl ether, the title compound, 2-[1-(4-fluorophenyl)-2,5-dioxo-3-[2-(thiophen-2-yl)ethyl] imidazolidin-4-yl]-N-(2-methoxypyrimidin-5-yl)acetamide, was obtained in 55% yield (143 mg) as beige solid. 1H-NMR (CDCl3): delta (ppm) 2.83 (m, 1H), 2.96 (m, 1H), 3.25 (m, 2H), 3.5 (m, 1H), 4.01 (m, 4H), 4.31 (m, 1H), 6.92 (m, 2H), 7.16 (m, 3H), 7.39 (m, 2H), 7.61 (s, 1H), 8.66 (m, 2H); MS (ESI+): m/z = 469.9 [M+H]+.
55%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide; at 20℃;	Example 80: Preparation of 2-[l-(4-fluorophenyl)-2,5-dioxo-3-[2-(thiophen-2- l)ethyl]imidazolidin-4-yl]-N-(2-methoxypyrimidin-5-yl)acetamide. TBTU (265.8 mg; 0.83 mmol; 1.5 eq), followed by DIPEA (288 mu 1-66 mmol; 3 eq) and after 10 minutes, <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong> (103.6 mg; 0.83 mmol; 1.5 eq) were added to a solution of 2-[l-(4-fluorophenyl)-2,5-dioxo-3-[2-(thiophen-2- yl)ethyl]imidazolidin-4-yl] acetic acid (1-17) (200 mg; 0.55 mmol; 1 eq) in dioxane/dimethylformamide (3 mL/300 mu). The reaction mixture was stirred at room temperature overnight. Saturated sodium hydrogenocarbonate (15 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with saturated sodium chloride (3 x 5 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel using dichloromethane/methanol (100/0 to 97/3) as an eluent. After washing in hydrochloric acid 1M and trituration in diethyl ether, the title compound, 2-[l-(4- fluorophenyl)-2,5-dioxo-3-[2-(thiophen-2-yl)ethyl]irnidazolidin-4-yl]-N-(2- methoxypyrimidin-5-yl)acetamide, was obtained in 55% yield (143 mg) as beige solid. 1H-NMR (CDC13): delta (ppm) 2.83 (m, 1H), 2.96 (m, 1H), 3.25 (m, 2H), 3.5 (m, 1H), 4.01 (m, 4H) , 4.31 (m, 1H) , 6.92 (m, 2H), 7.16 (m, 3H) , 7.39 (m, 2H), 7.61 (s, 1H) , 8.66 (m, 2H); MS (ESI+): m/z = 469.9 [M+H]+ .

Reference： [1]Patent: EP2664616,2013,A1 .Location in patent: Paragraph 0180-0181
[2]Patent: WO2013/171281,2013,A1 .Location in patent: Page/Page column 96-97

23
2-[1-(4-fluorophenyl)-5-oxo-2-sulfanylidene-3-[2-(thiophen-2-yl)ethyl]imidazolidin-4-yl]acetic acid [ No CAS ]
[ 56621-89-7 ]
2-[1-(4-fluorophenyl)-5-oxo-2-sulfanylidene-3-[2-(thiophen-2-yl)ethyl]imidazolidin-4-yl]-N-(2-methoxypyrimidin-5-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide; at 20℃;	Example 81 Preparation of 2-[1-(4-fluorophenyl)-5-oxo-2-sulfanylidene-3-[2-(thiophen-2-yl)ethyl]imidazolidin-4-yl]-N-(2-methoxypyrimidin-5-yl)acetamide. TBTU (254.5 mg; 0.79 mmol; 1.5 eq), followed by DIPEA (276 muL; 1.59 mmol; 3 eq) and after 10 minutes, <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong> (99.12 mg; 0.79 mmol; 1.5 eq) were added to a solution of 2-[1-(4-fluorophenyl)-5-oxo-2-sulfanylidene-3-[2-(thiophen-2-yl) ethyl]imidazolidin-4-yl]acetic acid (I-19) (200 mg; 0.53 mmol; 1 eq) in dioxane/dimethylformamide (3 mL/300 muL). The reaction mixture was stirred at room temperature overnight. Saturated sodium hydrogenocarbonate (15 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with saturated sodium chloride (3 x 5 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel using dichloromethane/methanol (100/0 to 98/2) as an eluent. After washing with 1M hydrochloric acid and trituration in diethyl ether, the title compound, 2-[1-(4-fluorophenyl)-5-oxo-2-sulfanylidene-3-[2-(thiophen-2-yl) ethyl]imidazolidin-4-yl]-N-(2-methoxypyrimidin-5-yl)acetamide, was obtained in 28 % yield (71 mg) as beige solid. 1H-NMR (DMSO-d6): delta (ppm) 3.2 (m, 4H), 3.75 (m, 1H), 3.88 (s, 3H), 4.26 (m, 1H), 4.75 (m, 1H), 6.97 (m, 2H), 7.37 (m, 5H), 8.71 (m, 2H), 10.47 (s, 1H); MS (ESI+): m/z = 485.8 [M+H]+.
28%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide; at 20℃;	Example 81: Preparation of 2-[l-(4-fluorophenyl)-5-oxo-2-sulfanylidene-3-[2- (thiophen-2-yl)ethyl]imidazolidin-4-yl]-N-(2-methoxypyrim TBTU (254.5 mg; 0.79 mmol; 1.5 eq), followed by DIPEA (276 mu 1-59 mmol; 3 eq) and after 10 minutes, <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong> (99.12 mg; 0.79 mmol; 1.5 eq) were added to a solution of 2-[l-(4-fluorophenyl)-5-oxo-2-sulfanylidene-3-[2- (thiophen-2-yl)ethyl]imidazolidin-4-yl]acetic acid (1-19) (200 mg; 0.53 mmol; 1 eq) in dioxane/dimethylformamide (3 mL/300 mu). The reaction mixture was stirred at room temperature overnight. Saturated sodium hydrogenocarbonate (15 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with saturated sodium chloride (3 x 5 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel using dichloromethane/methanol (100/0 to 98/2) as an eluent. After washing with 1M hydrochloric acid and trituration in diethyl ether, the title compound, 2-[l-(4- fluorophenyl)-5-oxo-2-sulfanylidene-3-[2-(thiophen-2-yl)ethyl]imidazolidin-4-yl]-N- (2-methoxypyrimidin-5-yl)acetamide, was obtained in 28% yield (71 mg) as beige solid. 1H-NMR (DMSO-d6): delta (ppm) 3.2 (m, 4H), 3.75 (m, 1H), 3.88 (s, 3H) , 4.26 (m, 1H), 4.75 (m, 1H), 6.97 (m, 2H) , 7.37 (m, 5H) , 8.71 (m, 2H) , 10.47 (s, 1H); MS (ESI+): m/z = 485.8 [M+H]+ .

Reference： [1]Patent: EP2664616,2013,A1 .Location in patent: Paragraph 0190-0191
[2]Patent: WO2013/171281,2013,A1 .Location in patent: Page/Page column 100-101

24
2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-1-(4-fluorophenyl)-2,5-dioxoimidazolidin-4-yl)acetic acid [ No CAS ]
[ 56621-89-7 ]
2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-1-(4-fluorophenyl)-2,5-dioxoimidazolidin-4-yl)-N-(2-methoxypyrimidin-5-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		c) 2-(3-{2-[4-(Dimethylamino)phenyl]ethyl}-1-(4-fluorophenyl)-2,5-dioxoimidazolidin-4-yl)-N-(2-methoxypyrimidin-5-yl)acetamide (example 78). [0255] TBTU (187.1 mg; 0.57 mmol; 1.5 eq) and DIPEA (131 muL; 0.75 mmol; 2 eq) were added to a solution of 2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-1-(4-fluorophenyl)-5-oxo-2-sulfanylideneimidazolidin-4-yl)acetic acid (1-39) (150 mg; 0.38 mmol; 1 eq) in dioxane (6 mL). The reaction mixture was stirred at room temperature for 30 minutes. Then, <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong> (93.8 mg; 0.75 mmol; 2 eq) in dimethylformamide (2 mL) was added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated to dryness. Saturated ammonium chloride was added (15 mL) and the aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with saturated sodium chloride (3 x 20 mL), dried over sodium sulfate and concentrated to dryness. The crude was purified by flash chromatography on silica gel using cyclohexane/ ethyl acetate (25/75 to 0/100) as an eluent. After trituration in diethyl ether/ dichloromethane/pentane, the title compound 2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-1-(4-fluorophenyl)-2,5-dioxoimidazolidin-4-yl)-N-(2-methoxypyrimidin-5-yl)acetamide was obtained in 33% yield (63.8 mg) as an off-white solid. 1H-NMR (DMSO-d6): delta (ppm) 2.69 (m, 1H), 2.80 (m, 1H), 2.83 (s, 6H), 3.02 (d, 1H), 3.12 (d, 1H), 3.28 (m, 1H), 3.68 (m, 1H), 3.88 (s, 3H), 4.51 (m, 1H), 6.64 (d, 2H), 7.05 (d, 2H), 7.36 (m, 4H), 8.71 (s, 2H), 10.39 (s, 1H); MS (ESI+): m/z = 506.9 [M+H]+.
33%		c) 2-(3-\|2-r4-(Dimethylamino)phenyllethyl)- l-(4-fluorophenyl)-2,5- dioxoimidazolidin-4-yl)-N-(2-methoxypyrimidin-5-yl)acetamide (example 78). TBTU (187.1 mg; 0.57 mmol; 1.5 eq) and DIPEA (131 mu 0.75 mmol; 2 eq) were added to a solution of 2-(3-{2-[4-(dimethylamino)phenyl]ethyl}-l-(4-fluorophenyl)- 5-oxo-2-sulfanylideneimidazolidin-4-yl)acetic acid (T39) (150 mg; 0.38 mmol; 1 eq) in dioxane (6 mL). The reaction mixture was stirred at room temperature for 30 minutes. Then, <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong> (93.8 mg; 0.75 mmol; 2 eq) in dimethylformamide (2 mL) was added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated to dryness. Saturated ammonium chloride was added (15 mL) and the aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with saturated sodium chloride (3 x 20 mL), dried over sodium sulfate and concentrated to dryness. The crude was purified by flash chromatography on silica gel using cyclohexane/ethyl acetate (25/75 to 0/100) as an eluent. After trituration in diethyl ether/dichloromethane/pentane, the title compound 2-(3-{2-[4- (dimethylamino)phenyl]ethyl}-l-(4-fluorophenyl)-2,5-dioxoimidazolidin-4-yl)-N-(2- methoxypyrimidin-5-yl)acetamide was obtained in 33% yield (63.8 mg) as an off- white solid. 1H-NMR (DMSO-d6): delta (ppm) 2.69 (m, 1H), 2.80 (m, 1H), 2.83 (s, 6H), 3.02 (d, 1H), 3.12 (d, 1H), 3.28 (m, 1H), 3.68 (m, 1H), 3.88 (s, 3H), 4.51 (m, 1H), 6.64 (d, 2H), 7.05 (d, 2H), 7.36 (m, 4H), 8.71 (s, 2H), 10.39 (s, 1H); MS (ESI+): m/z = 506.9 [M+H]+ .

Reference： [1]Patent: EP2664616,2013,A1 .Location in patent: Paragraph 0255-0256
[2]Patent: WO2013/171281,2013,A1 .Location in patent: Page/Page column 131-132

25
[ 2905-21-7 ]
[ 56621-89-7 ]
C₁₁H₁₀FN₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; at 100℃;	2-[(2-Chloro-6-fluorobenzyl)amino]-N-(2-methoxypyrimidin-5- yl)benzenesulfonamide (lntB2) The title compound (106 mg, impure, used without further purification) was prepared in two steps from 2-fluorobenzenesulfonyl chloride (0.46 mL, 3.5 mmol) and 5-amino- 2-methoxypyrimidine (482 mg, 3.85 mmol) in 1 ,4-dioxane at 100C; followed by 2- chloro-6-fluorobenzyl amine (0.36 mL, 2.8 mmol) in MeCN (1.5 mL) at 180C in a Biotage Initiator microwave reactor using the methods of (IntBI). LCMS (Method A): m/z 421.2, 423.2 (M-H)- (ES-), at 0.13 and 1.13 min, 95% TLC: Rf = 0.64 (iso-hexane:EtOAc)

Reference： [1]Patent: WO2014/6402,2014,A1 .Location in patent: Page/Page column 91

26
[ 1413913-54-8 ]
[ 56621-89-7 ]
[ 1569514-39-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 150℃; for 0.333333h;Microwave irradiation;	A mixture of 2-bromo-N-ieri-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3- b]pyrazine-7-carboxamide (150 mg, 351 muiotaetaomicron), <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong> (65.9 mg, 526 muiotaetaomicron), xantphos (60.9 mg, 105 muiotaetaomicron), Pd2(dba)3 (32.1 mg, 35.1 muiotaetaomicron) and cesium carbonate (229 mg, 702 muiotaetaomicron) in dioxane (2 mL) was heated in a microwave at 150C for 20 min. The mixture was cooled then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, 40-80 % ethyl acetate in hexanes) to give N-ieri-butyl- 2-(2-methoxypyrimidin-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3- b]pyrazine-7-carboxamide (99 mg, 210 muiotaetaomicron, 60 %) as a yellow solid. (EI/CI) m/z: 484.3 [M + H].

Reference： [1]Patent: WO2014/29732,2014,A1 .Location in patent: Page/Page column 66

27
[ 16885-99-7 ]
[ 79-37-8 ]
[ 56621-89-7 ]
2-(1-isopropyl-1H-indol-3-yl)-N-(2-methoxypyrimidin-5-yl)-2-oxoacetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9309 - 9333

28
[ 79-37-8 ]
[ 1158209-64-3 ]
[ 56621-89-7 ]
2-(1-(2-methoxyethyl)-1H-indol-3-yl)-N-(2-methoxypyrimidin-5-yl)-2-oxoacetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9309 - 9333

29
(+/-)-methyl 3-(5-amino-4-(diisobutylamino)-2-fluorophenyl)pentanoate [ No CAS ]
[ 7693-46-1 ]
[ 56621-89-7 ]
(+/-)-3-(4-(diisobutylamino)-2-fluoro-5-(3-(2-methoxypyrimidin-5-yl)ureido)phenyl)pentanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		To a homogeneous mixture of (+-)-methyl 3-(5-amino-4-(diisobutylamino)-2-fluorophenyl)pentanoate (compound 1128D, 25.4 mg, 0.07 mmol) in THF (1 mL), at room temperature in a sealable vial, was added 4-nitrophenyl carbonochloridate (25 mg, 0.12 mmol). The resulting mixture was stirred at ambient temperature for one hour before 4-ethoxy-2-fluoroaniline, HCl (41 mg, 0.22 mmol) and TEA (0.10 mL, 0.72 mmol) were added. The mixture was then stirred at 50 C. for 16 hours then at room temperature for two hours before MeOH (0.5 mL) was added to the reaction vial followed by LiOH (aq) (1M solution, 0.5 mL, 0.50 mmol). After 1.5 hours, the reaction was treated with LiOH (aq) (1M solution, 0.5 mL, 0.50 mmol) and stirred for 20 hours before being treated with acetic acid (0.06 mL, 1.05 mmol). The mixture was diluted with DMSO then purified by preparative RP HPLC (MeCN/H2O gradient+10-mM NH4OAc) to afford Example 1137 (22.6 mg, 60% yield); 12385] Example 1140 (25.7 mg, 73% yield) was preparedfollowing a procedure analogous to that for the synthesis ofExample 1137, except that <strong>[56621-89-7]2-methoxypyrimidin-5-amine</strong>(27.1 mg, 0.22 mmol) was used instead of 4-ethoxy-2-fluoroaniline, HC1. ?H NMR (500 MHz, DMSO-d5) oe 9.55(s, 1H), 8.66 (s, 2H), 7.85 (s, 1H), 7.80 (d, J=8.1 Hz, 1H),7.03 (d, J=11.9 Hz, 1H), 3.88 (s, 3H), 3.20-3.08 (m, 1H),2.75-2.61 (m, 4H), 2.58-2.54 (m, 2H), 1.71-1.59 (m, 3H),1.54-1.41 (m, 1H), 0.89-0.80 (m, 12H), 0.72 (t, J=7.3 Hz,3H). MS(ES): mlz=490 [M+H]. Tr=1.82 mm (Method C).

Reference： [1]Patent: US2016/289171,2016,A1 .Location in patent: Paragraph 2378; 2379; 2384; 2385

30
4-((4-(4-chloroquinolin-6-yl)phenyl)sulfonyl)morpholine [ No CAS ]
[ 56621-89-7 ]
N-(2-methoxypyrimidin-5-yl)-6-(4-(morpholinosulfonyl)phenyl)quinolin-4-amine [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 350 - 354

31
[ 40052-13-9 ]
[ 56621-89-7 ]
t-butyl 3-((2-methoxypyrimidin-5-yl)amino)-3-oxopropanoate [ No CAS ]