[ CAS No. 7709-13-9 ] {[proInfo.proName]}

Name: 7709-13-9|4-Chloro-1,3,5-triazin-2-amine|95%
Brand: Ambeed
SKU: A240713
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2D 3D

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Quality Control of [ 7709-13-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7709-13-9 ]

SDS Specification

Alternatived Products of [ 7709-13-9 ]

Product Details of [ 7709-13-9 ]

CAS No. :	7709-13-9	MDL No. :	MFCD19203794
Formula :	C₃H₃ClN₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ULVNIJSKNRGBHX-UHFFFAOYSA-N
M.W :	130.54	Pubchem ID :	24381
Synonyms :

Calculated chemistry of [ 7709-13-9 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	29.24
TPSA :	64.69 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) :	-6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.19
Log Po/w (XLOGP3) :	0.59
Log Po/w (WLOGP) :	0.12
Log Po/w (MLOGP) :	-0.9
Log Po/w (SILICOS-IT) :	0.75
Consensus Log Po/w :	0.35

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.58
Solubility :	3.47 mg/ml ; 0.0265 mol/l
Class :	Very soluble
Log S (Ali) :	-1.52
Solubility :	3.92 mg/ml ; 0.0301 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.5
Solubility :	4.13 mg/ml ; 0.0316 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 7709-13-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7709-13-9 ]

* 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 [ 7709-13-9 ]
Downstream synthetic route of [ 7709-13-9 ]

[ 7709-13-9 ] Synthesis Path-Upstream 1~3

1
[ 7709-13-9 ]
[ 931-86-2 ]

Reference： [1] Agricultural and Biological Chemistry, 1985, vol. 49, # 6, p. 1551 - 1558

2
[ 2831-66-5 ]
[ 7709-13-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	at -20℃; for 0.166667 h;	2,4-dichloro-l,3,5-triazine(45 mg, 0.3 mmol) was added to 2 mL of ΝΗ₄OH aq., the reaction was stirred at -20 °C for 10 min, then filtered, washed with water and dried to give 4-chloro- l,3,5-triazin-2-amine (18 mg, yield: 46percent) as a yellow solid which was used in the next step without further purification. MS (m/z): 131.0 (M+H)⁺.
46%	at -20℃; for 0.166667 h;	2,4-dichloro-1,3,5-triazine(45 mg, 0.3 mmol) was added to 2 mL of ΝΗ₄OH aq., the reaction was stirred at -20 °C for 10 min, then filtered, washed with water and dried to give 4-chloro- l,3,5-triazin-2-amine (18 mg, yield: 46percent) as a yellow solid which was used in the next step without further purification. MS (m/z): 131.0 (M+H)⁺.

Reference： [1] Patent: WO2014/15523, 2014, A1, . Location in patent: Page/Page column 126; 127
[2] Patent: WO2014/15830, 2014, A1, . Location in patent: Page/Page column 151
[3] Agricultural and Biological Chemistry, 1982, vol. 46, # 6, p. 1439 - 1445
[4] Patent: WO2011/146882, 2011, A1, . Location in patent: Page/Page column 108
[5] Patent: WO2014/15675, 2014, A1, . Location in patent: Page/Page column 151; 152
[6] Patent: WO2018/39972, 2018, A1, . Location in patent: Page/Page column 180

3
[ 1912-24-9 ]
[ 7709-13-9 ]

Reference： [1] Agricultural and Biological Chemistry, 1980, vol. 44, # 9, p. 2067 - 2072

[ 7709-13-9 ] Synthesis Path-Downstream 1~36

1
[ 1912-24-9 ]
[ 7709-13-9 ]

Reference： [1]Agricultural and Biological Chemistry,1980,vol. 44,p. 2067 - 2072

2
[ 67-56-1 ]
[ 7709-13-9 ]
[ 1122-73-2 ]

Reference： [1]Agricultural and Biological Chemistry,1980,vol. 44,p. 2067 - 2072

3
[ 124-41-4 ]
[ 7709-13-9 ]
[ 1122-73-2 ]

Reference： [1]Agricultural and Biological Chemistry,1980,vol. 44,p. 2067 - 2072

4
[ 7709-13-9 ]
[ 931-86-2 ]

Reference： [1]Agricultural and Biological Chemistry,1985,vol. 49,p. 1551 - 1558

5
[ 2831-66-5 ]
[ 7709-13-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	With ammonium hydroxide; at -20℃; for 0.166667h;	2,4-dichloro-l,3,5-triazine(45 mg, 0.3 mmol) was added to 2 mL of NuEta4OH aq., the reaction was stirred at -20 C for 10 min, then filtered, washed with water and dried to give 4-chloro- l,3,5-triazin-2-amine (18 mg, yield: 46%) as a yellow solid which was used in the next step without further purification. MS (m/z): 131.0 (M+H)+.
46%	With ammonium hydroxide; at -20℃; for 0.166667h;	2,4-dichloro-1,3,5-triazine(45 mg, 0.3 mmol) was added to 2 mL of NuEta4OH aq., the reaction was stirred at -20 C for 10 min, then filtered, washed with water and dried to give 4-chloro- l,3,5-triazin-2-amine (18 mg, yield: 46%) as a yellow solid which was used in the next step without further purification. MS (m/z): 131.0 (M+H)+.
	With ammonium hydroxide; at -20℃; for 0.166667h;	Method BGeneral conditions for the preparation of 4-chloro-l,3,5-triazin-2-amine:[00365] 2,4-Dichloro-l,3,5-triazine (B-1) (500 mg, 3.3 mmol, 1.0 eq) is dissolved in concentrated ammonium hydroxide (100 mL, 700 mmol, 212 eq) at -20 C and the resulting mixture is stirred at this temperature for 10 min. The mixture is then filtered, rinsed with water (5 mL x 3) and dried in vacuo to afford the product, 4-chloro- l,3,5-triazin-2-amine (B-2) as a solid.

	With ammonium hydroxide; at -20℃; for 0.166667h;	2,4-dichloro-l,3,5-triazine(45 mg, 0.3 mmol) was added to 2 mL of NuEta320 aq., the reaction was stirred at -20 C for 10 min, then filtered, washed with water and dried to give 4-chloro-l,3,5-triazin-2-amine (18 mg, yield: 46%) as a yellow solid which was used in the next step without further purification. MS (m/z): 131.0 (M+H)+.
	With ammonium hydroxide; at -20℃; for 0.166667h;	2,4-dichloro-1, 3, 5-triazine (8.0 g, 53.3 mmol) was added in portions to 200 mL of NH4OH at -20 .After addition, the mixture was stirred at -20 for 10mins, and then filtered, washed with water and dried to give 4-chloro-1, 3, 5-triazin-2-amine (5.7 g) as a yellow solid which was used to the next step without further purification. LC-MS: m/z 131.1 (M+H) +.

Reference： [1]Patent: WO2014/15523,2014,A1 .Location in patent: Page/Page column 126; 127
[2]Patent: WO2014/15830,2014,A1 .Location in patent: Page/Page column 151
[3]Agricultural and Biological Chemistry,1982,vol. 46,p. 1439 - 1445
[4]Patent: WO2011/146882,2011,A1 .Location in patent: Page/Page column 108
[5]Patent: WO2014/15675,2014,A1 .Location in patent: Page/Page column 151; 152
[6]Patent: WO2018/39972,2018,A1 .Location in patent: Page/Page column 180

8
[ 333408-31-4 ]
[ 7709-13-9 ]
[ 761446-44-0 ]
[ 1167546-76-0 ]

Yield	Reaction Conditions	Operation in experiment
16%		To a solution of (2-chloro-8-methylquinolin-3-yl)methanol (150 mg, 0.72 mmol) in 1 ,4-dioxane/water (4 mL/1 mL) was added l-methyl-4-(4,4,5,5-tetramethyl-[ 1,3,2]- dioxaborolan-2-yl)-lH-pyrazole (181 mg, 0.87 mmol), K2CO3 (199 mg, 1.44 mmol) and Pd(PPh3)4 (83 mg, 0.07 mmol). The mixture was degassed and heated in a microwave at 1500C for 1 h. The solvent was removed in vacuo and the residue dissolved in DCM (50 mL) and washed with water (2 x 10 mL). The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo. Purification by column chromatography (SiO2, 0-20% EtOAc in Et2O) afforded the desired intermediate. This was dissolved in 1,4-dioxane (6 mL) under nitrogen and to it was added NaH (55 mg, 1.36 mmol, 60% in mineral oil). The solution was stirred at r.t for 5 minutes before 4- chloro-l,3,5-triazin-2-amine (106 mg, 0.82 mmol) was added and the mixture heated at 800C for 48 h. The mixture was poured into EtOAc (50 mL) and washed with water (3 x 10 mL). Purification by column chromatography (SiO2, 2-6% MeOH in DCM) yielded the title compound (38 mg, 16%) as a white solid. deltaH (DMSO-J6) 8.42 (s, IH), 8.37 (s, IH), 8.34 (s, IH), 8.04 (s, IH), 7.83 (d, J 8.1 Hz, IH), 7.57-7.69 (m, 3H), 7.47 (t, J7.6 Hz, IH), 5.69 (s, 2H), 3.99 (s, 3H), 2.78 (s, 3H). LCMS (ES+) 348 (M+H)+, RT 2.75 minutes (Method T).

Reference： [1]Patent: WO2009/81105,2009,A2 .Location in patent: Page/Page column 109

9
[ 1167543-97-6 ]
[ 7709-13-9 ]
[ 1167546-85-1 ]

Yield	Reaction Conditions	Operation in experiment
26%		To a solution of Intermediate 107 (150 mg, 0.53 mmol) in 1,4-dioxane (6 niL) under nitrogen was added NaH (54 mg, 1.34 mmol, 60% in mineral oil). After stirring at r.t. for 5 minutes addition of 4-chloro-l,3,5-triazin-2-amine (104 mg, 0.80 mmol) took place and the reaction was heated at 8O0C for 48 h. The mixture was poured into EtOAc (50 mL) and washed with water (3 x 10 mL). The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo. Purification by column chromatography (SiO2, 50- 100% EtOAc in Petrol 40-60) yielded the title compound (52 mg, 26%) as a white solid. deltaH (CDCl3) 8.39 (s, IH), 8.37 (s, IH), 7.69 (d, J 8.1 Hz, IH), 7.58 (d, J7.0 Hz, IH), 7.38-7.48 (m, 2H), 7.26-7.29 (m, 2H), 7.02 (d, J 8.3 Hz, IH), 5.56 (s, 2H), 5.37 (br s, 2H), 3.87 (s, 3H), 2.82 (s, 3H). LCMS (ES+) 374 (M+H)+, RT 3.53 minutes {Method T).

Reference： [1]Patent: WO2009/81105,2009,A2 .Location in patent: Page/Page column 110

10
C₂₁H₃₀FN₃O₃ [ No CAS ]
[ 7709-13-9 ]
[ 1240185-81-2 ]

Yield	Reaction Conditions	Operation in experiment
34%		A mixture of Intermediate 16 (280 mg, 0.83 mmol), 3-methoxypropylamine (98 mg, 1.1 mmol) and DIPEA (0.4 mL, 2.19 mmol) in w-butanol (2 mL) was heated at 12O0C for 5 days. The reaction mixture was cooled and partitioned between water (30 mL) and EtOAc (100 mL). The organic layer was washed with water (5 x 20 mL), separated, dried (MgSO4) and concentrated in vacuo. The residue was then purified by column chromatography (SiO2, 75-100% EtOAc in isohexane) to give an off-white solid. This was dissolved in 1,4-dioxane (10 mL) and treated with HCl (2 mL; 4.0M in 1,4-dioxane) and the mixture was stirred at r.t. overnight. The reaction mixture was concentrated in vacuo to give an orange oil (200 mg, 81%). A portion of this oil (70 mg, 0.25 mmol), 2- amino-4-chloro-[l,3,5]triazine (35 mg, 0.27 mmol) and DIPEA (100 mg, 0.78 mmol) in w-butanol (2 mL) was heated at 1100C overnight. The solvent was removed in vacuo and the residue purified by preparative HPLC to give the title compound (31.5 mg, 34%) as a white solid. deltaH (CDCl3) 7.72 (IH, s), 7.37 (IH, dd, J 8.76, 6.25 Hz), 6.93 (IH, t, J 8.99 Hz), 6.43 (IH, s), 5.56-5.06 (4H, m), 3.89-3.34 (5H, m), 3.34 (3H, s), 2.53 (3H, d, J2.39 Hz), 2.03-1.92 (2H, m), 1.66 (3H, d, J 6.69 Hz). LCMS (ES+) 386 (M+H)+, 2.20 minutes (Method 2).

Reference： [1]Patent: WO2010/92340,2010,A1 .Location in patent: Page/Page column 97

11
[ 1240187-11-4 ]
[ 7709-13-9 ]
[ 1240184-92-2 ]

Yield	Reaction Conditions	Operation in experiment
24%		(2-Chloro-8-methylquinolin-3-yl)methanol (250 mg, 1.13 mmol), iV,iV-dimethyl-2- (methylamino)acetamide (658 mg, 5.66 mmol), DIPEA (1 mL, 5.66 mmol) and NMP (3 mL) were combined in a sealed tube and heated to 14O0C for 5 h. After cooling, the mixture was dissolved in a 1 :1 mixture Of Et2O and EtOAc (100 mL) and washed with saturated brine (3 x 25 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by chromatography (0-5% MeOH in DCM) gave a yellow solid (195 mg, 60%). LCMS (ES+) 288 (M+H)+. To the yellow solid (90 mg, 0.31 mmol) in 1,4-dioxane (3 mL) was added NaH (31 mg, 0.78 mmol; 60% dispersion in mineral oil). The reaction mixture was stirred at r.t. for 5 minutes. 2-Amino-4-chloro- [l,3,5]triazine (45 mg, 0.34 mmol) was added and the mixture was heated in a sealed tube at 800C overnight. After cooling, the mixture was diluted with water (10 mL) and extracted with DCM (3 x 20 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 0-5% MeOH in DCM) gave the title compound (28 mg, 24%) as a white solid. deltaH (DMSO-d6) 8.35 (IH, s), 8.20 (IH, s), 7.66-7.62 (3H, m), 7.47 (IH, d, J6.99 Hz), 7.22 (IH, t, J7.52 Hz), 5.48 (2H, s), 4.35 (2H, s), 3.20 (3H, s), 3.05 (3H, s), 2.86 (3H, s), 3H under H2O. LCMS (ES+) 382 (M+H)+, RT 3.07 minutes (Method 1).

Reference： [1]Patent: WO2010/92340,2010,A1 .Location in patent: Page/Page column 69-70

12
[ 1240186-32-6 ]
[ 7709-13-9 ]
[ 1240184-73-9 ]

Yield	Reaction Conditions	Operation in experiment
36%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 130℃; for 1.5h;Microwave Irradiation;	A mixture of Intermediate 25 (62 mg, 0.18 mmol), 2-amino-4-chloro-[l,3,5]- triazine (47 mg, 0.36 mmol) and DIPEA (0.15 mL, 0.89 mmol) in 1,4-dioxane (3 mL) was heated at 13O0C under microwave irradiation for 1.5 h. The reaction mixture was concentrated in vacuo and the residue purified by preparative HPLC to give the title compound (28.7 mg, 36%). deltaH (DMSO-de) 8.14-7.90 (2H, m), 7.73-7.64 (3H, m), 7.17 (IH, t, J 7.75 Hz), 7.28-6.72 (2H, m), 6.65-6.54 (IH, m), 5.33 (IH, br s), 4.33 (2H, br s), 3.92-3.79 (IH, m), 3.23 (IH, t, J 13.52 Hz), 2.92-2.70 (IH, m), 2.30-1.70 (5H, m), 1.56 (3H, s), 1.50-1.33 (2H, m). LCMS (ES+) 441 (M+H)+, RT 7.85 minutes (Method 5).

Reference： [1]Patent: WO2010/92340,2010,A1 .Location in patent: Page/Page column 61-62

13
[ 1242180-34-2 ]
[ 7709-13-9 ]
[ 1242179-37-8 ]

Yield	Reaction Conditions	Operation in experiment
22%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 150℃; for 1h;Microwave irradiation;	EXAMPLE 29j^-(4-{3-ri-(4-Amino-[l,3,511xiazin-2-ylamino^ethyl1-8-methylquinolin-2-v?piperazin- 1 -vDfcvclopropyDmethanoneIntermediate 47 (62 mg, 0.18 mmol) was dissolved in NMP (2 mL) and DIPEA (0.095 mL, 0.55 mmol) was added, followed by 2-amino-4-chloro-[l,3,5]triazine (28 mg, 0.22 mmol). The mixture was heated under microwave irradiation to 15O0C for 1 h. After cooling, the solvents were removed in vacuo. Purification by preparative HPLC gave the title compound (32 mg, 22%) as an off-white solid. deltaH (CDCl3) 8.15 (IH, s), 7.99 (IH, s), 7.54 (IH, d, J 8.0 Hz), 7.46 (IH, d, J 7.0 Hz), 7.34-7.27 (IH, m), 5.70-5.40 (2H, m), 4.95 (2H, br s), 4.10-3.00 (8H, m), 2.70 (3H, s), 1.84-1.79 (IH, m), 1.55 (3H, s), 1.06-1.01 (2H, m), 0.84-0.77 (2H, m). LCMS (ES+) 433 (M+H)+, RT 3.02 minutes {Method 2).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 82

14
(S)-ethyl 2-{4-[3-(1-aminoethyl)-8-chloroquinolin-2-yl]piperazin-1-yl}acetate bis hydrochloride [ No CAS ]
[ 7709-13-9 ]
[ 1242179-70-9 ]

Yield	Reaction Conditions	Operation in experiment
30%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 130℃; for 1h;Microwave irradiation;	EXAMPLE 62(iSVEthyl 2-(4- (3 - r 1 -C4-amino- [ 1 ,3.51triazin-2-ylaminotethvH -8-chloroquinolin-2- yl } piperazin- 1 -vDacetateA solution of Intermediate 57 (120 mg, 0.243 mmol), 2-amino-4-chloro- [l,3,5]triazine (38 mg, 0.292 mmol) and DIPEA (0.17 mL, 0.97 mmol) in 77-butanol (3 mL) was heated at 1300C under microwave irradiation for 1 h. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford the title compound (34 mg, 30%) as a white solid. deltaH (CDCl3) 8.13 (IH, s), 7.96 (IH, s), 7.68 (IH, dd, J7.51, 1.34 Hz), 7.57 (IH, dd, J 8.08, 1.34 Hz), 7.26 (IH, m), 5.73-5.75 (IH, m), 5.53-5.37 (2H, m), 5.09-4.93 (IH, m), 4.22 (2H, q, J7.13 Hz), 3.81-3.72 (3H, m), 3.44-3.28 (5H, m), 3.00-2.73 (5H, m), 1.30 (3H, t, J7.13 Hz). LCMS (ES+) 471 (M+H)+, 7.27 minutes (Method 8).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 97

15
[ 1242180-47-7 ]
[ 7709-13-9 ]
[ 1242179-57-2 ]

Yield	Reaction Conditions	Operation in experiment
9.6%	With sodium hydride; In N,N-dimethyl-formamide; at 80℃;	EXAMPLE 494-[8-Methyl-2-(pyrrolidin-l-yl)quiiiolin-3-yl]methoxy}-["l,3,51triazin-2-amineIntermediate 60 (100 mg, 0.39 mmol) and 2-amino-4-chloro-[l,3,5]triazine (61 mg, 0.47 mmol) were combined in DMF (2 mL). NaH (60% suspension in mineral oil, 34 mg, 0.86 mmol) was added and the resulting mixture was heated at 8O0C overnight. After cooling, Et2O (10 mL) was added and the mixture was washed with water and brine. The organic layer was dried (MgSO4), filtered and the solvent was removed in vacuo. Purification by column chromatography on silica, eluting with 30-50% EtOAc in isohexane, gave the title compound (9.1 mg, 9.6%). deltaH (CDCl3) 8.41 (IH, s), 8.02 (IH, s), 7.49-7.37 (2H, m), 7.11 (IH, t, J7.50 Hz), 5.50 (2H, s), 3.75 (4H, t, J6.27 Hz), 2.64 (2H, s), 2.03-1.96 (4H, m), 1.90-1.74 (3H, m). LCMS (ES+) 337 (M+H)+, RT 3.93 minutes (Method 1).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 92

16
[ 1242180-48-8 ]
[ 7709-13-9 ]
[ 1242179-58-3 ]

Yield	Reaction Conditions	Operation in experiment
1.8%	With sodium hydride; In 1,4-dioxane; at 80℃;	EXAMPLE 504-{r8-Methyl-2-(morpholin-4-yl)quinolin-3-yllmethoxyl-ri,3,5]triazin-2-amineIntermediate 61 (200 mg, 0.78 mmol) and 2-amino-4-chloro-[l,3,5]triazine (120 mg, 0.93 mmol) were combined in 1,4-dioxane (3 mL). NaH (60% suspension in mineral oil, 37 mg, 0.93 mmol) was added and the resulting mixture was heated at 8O0C overnight. After cooling, Et2O (10 mL) was added and the mixture was washed with water and brine. The organic layer was dried (MgSO4), filtered and the solvent was removed in vacuo. Purification by column chromatography on silica, eluting with 50- 100% EtOAc in isohexane, gave the title compound (5.1 mg, 1.8%). deltaH (CDCl3) 8.43 (IH, s), 8.21 (IH, s), 7.56 (IH, d, J8.1 Hz), 7.48 (IH, d, J7.0 Hz), 7.29 (IH, d, J7.6 Hz), 5.55 (2H5 s), 5.37 (2H, s), 3.92 (4H5 1, J4.55 Hz), 3.38 (4H5 t, J4.56 Hz)5 2.71 (3H5 s). LCMS (ES+) 353 (M+H)+, RT 3.47 minutes {Method 1).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 92; 93

17
[ 1242180-51-3 ]
[ 7709-13-9 ]
[ 1242179-59-4 ]

Yield	Reaction Conditions	Operation in experiment
16%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 150℃; for 1h;Microwave irradiation;	EXAMPLE 514-{3-r('4-Amino-['l,3,51triazin-2-ylamino')methyll-8-methylquinolm-2-yl}piperazin-2-oneIntermediate 65 (100 mg, 0.37 mmol) was dissolved in NMP (1.5 niL). DIPEA (0.32 niL, 0.19 mmol) was added, followed by 2-amino-4-chloro-[l,355]triazine (97 mg, 0.74 mmol). The mixture was heated under microwave irradiation to 15O0C for 1 h. After cooling, the solvents were removed in vacuo. Purification by preparative HPLC gave the title compound (21 mg, 16 %) as a pale brown solid. 6H (DMSOd6) 8.08 (IH, s), 8.03 (IH, s), 7.95 (IH5 d, J 14.44 Hz)5 7.89 (IH, s), 7.75-7.65 (IH5 m), 7.52 (IH, d, J 6.98 Hz), 7.32 (IH5 1, J7.54 Hz), 6.88 (2H, m), 4.68-4.60 (2H5 m), 4.03 (IH, s), 3.94 (IH5 s), 3.51 (2H, s), 3.39-3.35 (2H, m), 2.66 (3H5 s). LCMS (ES+) 365 (M+H)+, RT 7.22 minutes {Method 8).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 93

18
[ 1242180-53-5 ]
[ 7709-13-9 ]
[ 1242179-61-8 ]

Yield	Reaction Conditions	Operation in experiment
35%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 120℃; for 1h;Microwave irradiation; Sealed tube;	EXAMPLE 53(^-l-^-fS-ri-^-Amino-ri.S^itriazin^-ylamino^ethvn-delta-methylquinolin^-vU- piperazin- 1 -y DethanoneIntermediate 67 (100 mg, 0.32 mmol), 2-amino-4-chloro-[l,3,5]triazine (50 mg, 0.38 mmol), DIPEA (0.29 mL, 1.60 mmol) and NMP (2 mL) were combined in a sealed tube and heated under microwave irradiation to 12O0C for 1 h. After cooling, the reaction mixture was dissolved in a 1 :1 mixture of EtOAc and Et2O (200 mL) and washed with saturated brine (3 x 50 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Purification by column chromatography on silica, eluting with 10% MeOH in DCM, afforded the title compound (45 mg, 35%) as a white solid. deltaH (CDCl3) 8.15-8.05 (IH, m), 8.05-7.95 (IH, m), 7.53 (IH, d, J 8.05 Hz), 7.47 (IH5 d, J 8.05 Hz), 7.33-7.27 (IH, m), 6.55-6.50 (IH, m), 5.62-5.40 (3H, m), 4.00-3.86 (IH, m), 3.85-3.65 (3H, m), 3.61 (2H, d, J 10.77 Hz), 3.30-3.16 (IH, m), 3.15-3.05 (IH, m), 2.71 (3H, s), 2.16 (3H, s), 1.54 (3H, d, J 6.57 Hz). LCMS (ES+) 407 (M+H)+, RT 2.80 minutes {Method 1).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 93; 94

19
[ 1242180-54-6 ]
[ 7709-13-9 ]
[ 1242179-62-9 ]

Yield	Reaction Conditions	Operation in experiment
49%		EXAMPLE 544-{3-rf4-Amino-ri,3,5]triazin-2-yloxy^methyll-8-methylquinolin-2-vUpiperazin-2-one Intermediate 68 (80 mg, 0.29 mmol) was suspended in 1,4-dioxane (5 mL) and NaH (30 mg, 0.74 mmol; 60% dispersion in mineral oil) was added. The reaction mixture was heated at 8O0C for 15 minutes. 2-Amino-4-chloro-[l,3,5]triazine (58 mg, 0.44 mmol) was added and the mixture was heated at 800C for a further 5 h. After cooling, the mixture was dissolved in EtOAc (100 mL) and washed with water (20 mL) and brine (20 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography on silica, eluting with 0-10% MeOH in DCM, afforded the title compound (52 mg, 49%) as a cream solid. deltaH (DMSO-d6) 8.34 (2H, d, J 8.71 Hz), 7.95 (IH, s), 7.76 (IH, d, J 8.02 Hz), 7.64 (IH, s), 7.61-7.55 (2H, m), 7.37 (IH, t, J7.53 Hz), 5.54 (2H, s), 3.97 (2H, s), 3.56 (2H, t, J5.24 Hz), 2.67 (3H, s), 2.54 (2H, under DMSO). LCMS (ES+) 366 (M+H)+, RT 2.44 minutes {Method 1).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 94

20
(S)-2-(4-[3-(1-aminoethyl)-8-chloroquinolin-2-yl]piperazin-1-yl)ethanol bis hydrochloride [ No CAS ]
[ 7709-13-9 ]
[ 1242179-76-5 ]

Yield	Reaction Conditions	Operation in experiment
48%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 140℃; for 1h;Microwave irradiation; Sealed tube;	EXAMPLE 68(^-2-r4-l3-ri-r4-Amino-ri,3,51triazin-2-ylaminoN)etliyl1-8-chloiOquinolin-2-vUpiperazin- 1-yliethanolIntermediate 75 (65 mg, 0.17 mmol), w-butanol (5 mL), DIPEA (1 mL) and 2- amino-4-chloro-[l53,5]triazine (30 mg, 0.23 mmol) were combined in a sealed tube and heated under microwave irradiation to 1400C for 1 h. The reaction mixture was then concentrated and purified by preparative HPLC to give the title compound (33.4 mg, 48%) as an off-white solid. deltaH (DMSO-J6) 8.27-8.20 (IH, m), 8.02 (IH, s), 7.96-7.79 (2H, m), 7.39 (IH, t, J 7.80 Hz), 7.00-6.40 (3H, br m), 5.43-5.35 (IH, m), 4.50-4.40 (IH5 m), 3.75-3.52 (4H, m), 3.18-3.11 (2H5 m), 2.78-2.51 (4H, m), 1.41 (3H, d, J 6.54 Hz)5 2H under H2O peak. LCMS (ES+) 429 (M+H)+5 6.95 minutes {Method 8).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 100

21
[ 1242180-63-7 ]
[ 7709-13-9 ]
[ 1242179-78-7 ]

Yield	Reaction Conditions	Operation in experiment
21%		EXAMPLE 70r^-l-r4-{3-ri-r4-Amino-ri3,51triazin-2-ylamino)ethyll-7-fluoro-8-methylquinolin-2- yl}piperazin-l-ylV2-hvdroxyethanoneIntermediate 76 (43 mg, 0.09 mmol), MeOH (5 niL) and HCl (2N in Et2O, 2 niL) were combined and stirred at r.t. for 5 h. The reaction mixture was then concentrated to dryness. The resulting material (40 mg), rc-butanol (6 mL), DIPEA (1 mL) and 2-amino- 4-chloro-[l,3,5]triazine (45 mg, 0.35 mmol) were combined and heated under microwave irradiation to 15O0C for 40 minutes. The reaction mixture was then concentrated and purified by preparative HPLC to give the title compound (8.19 mg, 21%) as an off-white solid. deltaH (DMS(W6) 8.26 (IH, d, J7.72 Hz), 8.04-7.93 (IH, m), 7.77-7.71 (IH, m), 7.33 (IH, t, J9.l l Hz), 5.48-5.41 (IH, m), 4.68-4.60 (IH, m), 4.22-4.17 (2H, m), 3.88-3.46 (7H, m), 3.18-2.97 (3H, m), 1.42 (3H, d, J 6.58 Hz), 3 NH and OH not visible. LCMS (ES+) 441 (MfH)+, 9.92 minutes {Method 9).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 101

22
[ 1242180-83-1 ]
[ 7709-13-9 ]
[ 1242179-89-0 ]

Yield	Reaction Conditions	Operation in experiment
11%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 130℃; for 1.5h;Microwave irradiation;	EXAMPLE 81(y)-4-{3-ri-(4-Amino-[l,3,51triazin-2-ylamino)ethyl]-8-bromoquinolm-2-yl}piperazin-2- oneTo a solution of Intermediate 95 (35 mg, 0.10 mmol) in dry n-butanol (1.5 mL) were added 2-amino-4-chloro-[l,3,5]triazine (20 mg, 0.15 mmol) and DIPEA (0.09 mL, 0.5 mmol). The reaction mixture was heated at 1300C under microwave irradiation for 90 minutes. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford the title compound (6 mg, 11%) as an off-white solid, delta? (MeOD-^4) 8.26 (IH5 s), 8.05 (IH5 s), 7.96 (IH5 d, J 7.53 Hz)5 7.79 (IH5 d, J 7.91 Hz)5 7.32 (IH, t, J 7.8 Hz)5 5.60-5.45 (IH5 m), 4.50 (IH, d, J 17.6 Hz)5 4.39 (IH, d, J 18.4 Hz), 4.15-4.08 (2H5 m), 3.60-3.52 (IH5 m), 3.48-3.40 (IH, m), 1.49 (3H5 d, J6.87 Hz). LCMS (ES+) 443, 445 (M+H)+, 2.60 minutes (Method 1).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 106

23
[ 1242180-88-6 ]
[ 7709-13-9 ]
[ 1242179-98-1 ]

Yield	Reaction Conditions	Operation in experiment
7%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 150℃; for 1h;Microwave irradiation;	EXAMPLE 90N2 -US)- 1 - ( 8-Chloro-2- [(,y)-2-(methoxymethyl)pyrrolidin- 1 -yllquinolin-3 -vU ethyl] - [1,3 ,5]triazine-2,4-diamineIntermediate 99 (53 mg, 0.166 mmol), 2-amino-4-chloro-[l,3,5]triazine (32 mg, 0.246 mmol), DIPEA (0.090 mL, 0.50 mmol) and NMP (1 mL) were combined and heated under microwave irradiation at 15O0C for 1 h. After cooling, the mixture was dissolved in a 1 : 1 mixture of EtOAc and Et2O (200 mL) and washed with saturated brine (3 x 30 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. Purification by preparative HPLC followed by column chromatography (SiO2, 96:3:1 DCM/MeOH/NH3 in MeOH) gave the title compound (4.6 mg, 7%) as an off- white solid. deltaH (CDCl3) 8.18 (IH, s), 7.89 (IH, s), 7.66-7.62 (IH, m), 7.51 (IH, dd, J 8.01, 1.36 Hz), 7.14 (IH, t, J7.69 Hz), 5.65-5.31 (2H, m), 5.02-4.88 (4H, m), 3.86-3.61 (3H, m), 3.55-3.50 (IH, m), 3.38 (3H, s), 2.29-2.25 (IH, m), 2.10-1.85 (2H, m), 1.41 (3H, d, J 6.66 Hz), NH not visible. LCMS (ES+) 414 (M+H)+, 2.55 minutes {Method 2).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 111

24
[ 1242180-92-2 ]
[ 7709-13-9 ]
[ 1242180-01-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 140℃; for 0.833333h;Microwave irradiation;	EXAMPLE 934- { 3 - ["(4- Amino-[ 1 ,3 ,51triazin-2-ylamino)methyl1 -8-chloroqumolm-2-yl}piperazin-2-one Intermediate 103 (90 mg, 0.31 mmol) was dissolved in NMP (1.5 mL) and treated with DIPEA (0.27 mL, 0.15 mmol) followed by 2-amino-4-chloro-[l,3,5]triazine (60 mg, 0.47 mmol). The mixture was heated under microwave irradiation to 14O0C for 50 minutes. The crude reaction mixture was purified by preparative HPLC to give the title compound (60 mg, 50%) as an off-white solid. deltaH (DMSO-<;i6) 8.17 (IH, s), 8.09-8.00 (2H, m), 7.92 (IH, s), 7.87 (IH, d, J 8.10 Hz), 7.82 (IH, d, J7.54 Hz), 7.39 (IH, t, J7.82 Hz), 6.90 (2H, s), 4.67-4.57 (2H5 m), 3.60-3.56 (2H, m), 3.52-3.47 (2H, m), 3.45-3.40 (2H, m). LCMS (ES+) 385 (M+H)+, 8.01 minutes (Method 9).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 112

25
[ 1242180-04-6 ]
[ 7709-13-9 ]
[ 1242179-21-0 ]

Yield	Reaction Conditions	Operation in experiment
5%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 100℃;	EXAMPLE 13(iotaS)-4-{3-[l-(4-Amino-[l,3,51triazin-2-ylamino)ethyl1-8-methylquinolin-2-yl>;piperazin-2- oneTo a solution of Intermediate 7 (100 mg, 0.35 mmol) in n-butanol (2.0 mL) was added 2-amino-4-chloro-[l,3,5]tiazine (50 mg, 0.37 mmol) and DIPEA (0.1 mL, 0.7 mmol). The reaction mixture was heated at 1000C overnight. The solvent was removed in vacuo and the residue purified by preparative HPLC to give the title compound (6 mg, 5%) as an off-white solid. deltaH (CDCl3) 8.11 (IH, s), 8.02 (IH, s), 7.51 (IH, d, J8.0 Hz), 7.44 (IH, d, J7.0 Hz), 7.31-7.21 (IH, m), 6.23-6.05 (2H, m), 5.41 (IH, m), 5.12 (IH, d, J 17.5 Hz), 4.67 (IH, d, J 17.4 Hz), 4.32-4.22 (IH, m), 4.11-4.02 (IH, m), 3.60-3.45 (2H, m), 2.68 (3H, s), 1.79 (2H, s), 1.40 (3H, d, J 6.6 Hz). LCMS (ES+) 379 (M+H)+, RT 14.58 minutes (Method 6).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 75

26
C₂₂H₃₀N₄O₃ [ No CAS ]
[ 7709-13-9 ]
[ 1242179-40-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 32l-rS-iri^-l-r^-Amino-rLS^ltriazin^-vDaminolethvU-delta-methylquinolin^-vD-ClLambdal- diazepan-5-oneA mixture of Intermediate 4 (100 mg, 0.31 mmol), [l,4]diazepan-5-one (178 mg, 1.56 mmol) and DIPEA (0.28 mL, 1.56 mmol) in NMP (3 mL) was heated at 14O0C for 4 days. The mixture was poured into water (10 mL) and the aqueous extracted with DCM (2 x 50 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography on silica, eluting with 5% MeOH in DCM, to give an orange oil. This oil was dissolved in DCM (5 mL) and to this solution was added TFA (2 mL). The mixture was stirred at r.t. for 1 h and the solvent removed in vacuo. To a portion (50 mg, 0.17 mmol) of the resulting product in «-butanol (2 mL) were added 2-amino-4-chloro-[l,3,5]triazine (40 mg, 0.33 mmol) and DIPEA (0.8 mL, 0.65 mmol) and the mixture was heated at 12O0C overnight. Purification by column chromatography on silica, eluting with 5% methanolic ammonia in DCM, afforded the title compound (15 mg, 20%) as a pale yellow solid. deltaH (MeOD-d4) 8.16 (IH, s), 8.08-7.97 (IH, m), 7.60 (IH, d, J8.1 Hz), 7.47 (IH, d, J7.0 Hz), 7.30 (IH, t, J7.5 Hz), 5.58-5.52 (IH, m), 3.83-3.24 (6H, m), 3.03-2.92 (IH, m), 2.89-2.78 (IH, m), 2.69 (3H5 s), 1.57-1.51 (3H5 m). LCMS (ES+) 393 (M+H)+, RT 12.10 minutes (Method 5).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 83; 84

27
C₂₀H₂₆FN₃O₂ [ No CAS ]
[ 7709-13-9 ]
[ 1242179-51-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 43N-UlS)-I- r7-Fruoro-2-Cpyrrolidin- 1 -vDquinolin-3 -yli ethyl >; - 1.3.5"ltriazine-2.4-diammeA mixture of Intermediate 26 (324 mg, 1.0 mmol), pyrrolidine (142 mg, 2.0 mmol) and DIPEA (0.28 mL, 2.0 mmol) in w-butanol (2 mL) was heated at 12O0C for 3 days. The solvent was removed in vacuo and the residue purified by column chromatography on silica, eluting with Et2O, to give a yellow oil. This was dissolved in MeOH (5 mL) and to this solution was added 4M HCl in 1,4-dioxane (2 mL). The mixture was stirred at r.t. overnight and the solvent removed in vacuo. To a portion (100 mg, 0.39 rnmol) of the resulting product in w-butanol (2 mL) were added 2-amino-4- chloro-[l,3,5]triazine (55 mg, 0.43 mmol) and DIPEA (0.2 mL) and the mixture was heated at HO0C overnight. Purification by preparative HPLC afforded the title compound (14 mg, 8%) as an off-white solid. deltaH (CDCl3) 8.20-8.13 (IH, m), 7.86 (IH, s), 7.54 (IH, dd, J 8.8, 6.3 Hz), 7.34 (IH, dd, J 10.9, 2.6 Hz), 7.00-6.94 (IH, m), 5.57-5.42 (IH, m), 5.00 (2H, br s), 3.81-3.74 (2H, m), 3.76-3.64 (3H, m), 2.09-1.88 (4H, m), 1.48 (3H, d, J 6.21 Hz). LCMS (ES+) 354 (M+H)+, RT 17.54 minutes {Method 6).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 88; 89

28
C₂₃H₃₁FN₄O₃ [ No CAS ]
[ 7709-13-9 ]
[ 1242179-52-7 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 44iV-ri-('3-{riy)-l-r('4-Amino-ri,3,51triazin-2-v?aminolethvU-7-fluoroquinolin-2-ylV piperidin-4-yl] acetamideA mixture of Intermediate 26 (324 mg, 1.0 mmol), 4-(acetylamino)piperidine (284 mg, 2.0 mmol) and DIPEA (0.28 mL, 2.0 mmol) in ?-butanol (2 mL) was heated at 12O0C for 3 days. The solvent was removed in vacuo and the residue purified by column chromatography on silica, eluting with Et2O, to give a yellow oil. This was dissolved in MeOH (5 mL) and to this solution was added 4M HCl in 1,4-dioxane (2 mL). The mixture was stirred at r.t. overnight and the solvent removed in vacuo. To a portion (100 mg, 0.3 mmol) of the resulting product in r°-butanol (2 mL) were added 2-amino-4- chloro-[l,3,5]triazine (44 mg, 0.34 mmol) and DIPEA (0.2 mL) and the mixture was heated at HO0C overnight. Purification by preparative HPLC afforded the title compound (40 mg, 18%) as a pale yellow solid. deltaH (CDCl3) 8.11 (IH, s), 7.95 (IH, s), 7.63 (IH, dd, J8.9, 6.1 Hz), 7.49 (IH, dd, 710.4, 2.5 Hz), 7.15 (IH, m), 6.06 (IH, s), 5.53 (IH, s), 5.37 (IH, s), 5.20 (2H, s), 4.07-3.98 (IH, m), 3.88 (IH, s), 3.49 (IH, m), 3.32 (IH, t, J 11.7 Hz), 2.92 (IH, t, .711.5 Hz), 2.17-2.07 (2H, m), 2.17-1.90 (3H, m), 1.78-1.58 (2H, m), 1.51 (3H, d, J 6.7 Hz). LCMS (ES+) 425 (M+H)+, RT 7.08 minutes {Method 8).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 89

29
C₂₂H₂₉FN₄O₃ [ No CAS ]
[ 7709-13-9 ]
[ 1242179-56-1 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 48l-r4-r3-{ri^-l-r(4-Amino-ri.3,51triazin-2-yl)aminolethvU-7-fluoroquinolm-2-yl)- piperazin- 1 - yl] ethanoneA mixture of Intermediate 26 (324 mg, 1.0 mmol), 1-acetylpiperazine (256 mg, 2.0 mmol) and DIPEA (0.28 mL, 2.0 mmol) in 77-butanol (2 mL) was heated at 12O0C for 3 days. The solvent was removed in vacuo and the residue purified by column chromatography on silica, eluting with Et2O, to give a yellow oil. This was dissolved in MeOH (5 mL) and to this solution was added 4M HCl in 1,4-dioxane (2 mL). The mixture was stirred at r.t. overnight and the solvent removed in vacuo. To a portion (100 mg, 0.31 mmol) of the resulting product in r°~butanol (1 mL) were added 2-amino-4- chloro-[l,3,5]triazine (45 mg, 0.34 mmol) and DIPEA (0.2 mL) and the mixture was heated at 16O0C under microwave irradiation for 1 h. Purification by preparative HPLC afforded the title compound (11 mg, 9%) as an off-white solid. deltaH (CDCl3) 8.19 (IH, s), 8.01 (IH, s), 7.67 (IH, dd, J8.9, 6.0 Hz), 7.50 (IH, dd, J 10.3, 2.5 Hz), 7.18 (IH, td, J 8.6, 2.6 Hz), 5.71-5.04 (3H, m), 3.93-3.47 (6H, m), 3.27-2.97 (2H, m), 2.16 (3H, s), 1.52 (3H, d, J 6.6 Hz). LCMS (ES+) 411 (M+H)+, RT 14.46 minutes (Method 6).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 91; 92

30
[ 1242181-07-2 ]
[ 7709-13-9 ]
[ 1242179-96-9 ]

Yield	Reaction Conditions	Operation in experiment
20%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 130℃; for 1h;Microwave irradiation;	EXAMPLE 88f6f)-Methyl 4-(3-ri-(4-amino-[1.3.51triazin-2-ylamino')ethyll-7-fluoro-8-methylquinolin- 2-yljpiperazine- 1 -carboxylateA solution of Intermediate 27 (501 mg, 1.479 mmol), methyl piperazine-1- carboxylate (981 mg, 6.802 mmol) and DIPEA (1.288 mL, 7.394 mmol) in NMP (3 mL) was heated under microwave irradiation at 13O0C for 4.5 h. After cooling, the mixture was dissolved in a 1:1 mixture of EtOAc and Et2O (250 rnL) and washed with saturated brine (3 x 50 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 10% EtOAc in DCM) gave a pale yellow oil (400 mg, 60%). LCMS (ES+) 447 (M+H)+. To the oil (400 mg, 0.896 mmol) dissolved in DCM (23 mL) was added TFA (4.1 mL). The reaction mixture was stirred at r.t. for 1.5 h. The excess solvent was removed in vacuo. The oil obtained was basified with 0.2M NaOH (40 mL) and extracted with EtOAc (3 x 80 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 95:4:1 DCM/MeOH/NH3 solution in MeOH) gave a colourless gum (278 mg, 90%). LCMS (ES+) 347 (M+H)+. The colourless gum (55.6 mg, 0.161 mmol), 2-amino-4-chloro-[l,3,5]triazine (31.4 mg, 0.241 mmol), DIPEA (0.084 mL, 0.482 mmol) and ??-BuOH (1 mL) were combined and heated under microwave irradiation at 13O0C for 1 h. Purification by preparative HPLC gave the title compound (14.4 mg, 20%) as a white solid. deltaH (DMSO-(Z6) 8.25 (IH, d, J 12.60 Hz), 8.02 (IH, d, J 10.06 Hz), 7.95 (IH, d, J 8.01 Hz), 7.74 (IH, dd, J 8.90, 6.24 Hz), 7.33 (IH, t, J9.13 Hz), 6.78 (2H, d, J68.59 Hz), 5.41 (IH, s), 3.83-3.59 (3H, m), 3.62-3.56 (4H, m), 3.10-3.04 (3H, m), 2.56 (4H, m), 1.41 (3H, d, J6.65 Hz). LCMS (ES+) 441 (M+H)+, 8.52 minutes (Method 8).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 109; 110

31
[ 1242180-06-8 ]
[ 7709-13-9 ]
[ 1242179-12-9 ]

Yield	Reaction Conditions	Operation in experiment
38%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 120℃; for 1h;Microwave irradiation;	EXAMPLE 4iV^r^-l-fdelta-ChloiO-Sigma-rr^-S-methylmorDholin^-yliquinolin-S-vnethyll-rLS.Sltriazine- 2,4-diamineA solution/suspension of Intermediate 13 (35 mg, 0.09 mmol), 2-amino-4-chloro- [l,3,5]triazine (18 mg, 0.14 mmol) and DIPEA (0.10 mL, 0.46 mmol) in o-butanol (1.5 mL) was heated at 12O0C under microwave irradiation for 1 h. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford the title compound (14 mg, 38%) as an off-white solid. deltaH (MeOD-d4) 8.27 (IH, s), 8.00 (IH, s), 7.76 (2H, t), 7.38 (IH, t), 5.66 (IH, m), 4.05-3.98 (IH, m), 3.94-3.81 (3H, m), 3.46 (IH, m), 3.35 (2H, under MeOD), 1.60 (3H, d), 1.15 (3H, d) (3 NH missing, 2H morph under MeOH). LCMS (ES+) 400 (M+H)+, RT 2.63 minutes (Method 2).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 71

32
[ 1242180-16-0 ]
[ 7709-13-9 ]
[ 1242179-24-3 ]

Yield	Reaction Conditions	Operation in experiment
16%		EXAMPLE 16(^-4-{3-ri-f4-Amino-ri.3.51triazin-2-ylamino^)ethyll-7-fluoro-8-methylquinolin-2- yl >; piperazin-2-oneTo a solution of Intermediate 29 (270 mg, 0.67 mmol) in MeOH (2 mL) was added hydrogen chloride (1 mL; 4N solution in 1,4-dioxane) and the mixture was stirred at r.t. overnight. The solvents were removed in vacuo to give 200 mg of a mauve solid. Half of this solid was dissolved in «-butanol (2 mL). DIPEA (0.1 mL, 0.78 mmol) and 2- amino-4-chloro-[l,3,5]triazine (52 mg, 0.4 mmol) were added and the resulting solution was heated at HO0C overnight. The solvent was removed in vacuo and the residue was purified by preparative HPLC to give the title compound (20 mg, 16%) as an off-white solid. deltaH (CDCl3) 8.09 (IH, s), 7.99 (IH, s), 7.45 (IH, dd, J8.9, 6.1 Hz), 7.10 (IH, t, J 9.0 Hz), 6.70 (IH, d, J7.0 Hz), 6.40 (IH, br s), 5.44-5.35 (2H, m), 5.19 (IH, d, J 17.5 Hz), 4.68 (IH, d, J 17.5 Hz), 4.28-4.17 (IH, m), 4.14-4.06 (IH, m), 3.60-3.51 (2H, m), 2.57 (3H, s), 1.39 (3H, d, J 6.6 Hz). LCMS (ES+) 397 (M+H)+, RT 2.28 minutes (Method 2).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 76; 77

33
[ 1242180-17-1 ]
[ 7709-13-9 ]
[ 1242179-22-1 ]

Yield	Reaction Conditions	Operation in experiment
13%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 120℃; for 1h;Microwave irradiation;	EXAMPLE 14(6r)-4-{3-ri-(4-Amino-[L3,51triazin-2-ylaminoN)ethvn-8-chloroquinolin-2-vUrhoirhoerazin-2- oneTo a solution of Intermediate 30 (120 mg, 0.39 mmol) in r°-butanol (2.5 mL) was added 2-amino-4-chloro-[l,3,5]triazine (95 mg, 0.79 mmol) and DIPEA (0.14 mL, 0.79 mmol). The reaction mixture was heated at 12O0C under microwave irradiation for 1 h. The solvent was removed in vacuo and the residue purified by preparative HPLC followed by chromatography on an SCX column, eluting with IM NH3 in MeOH, to give the title compound (20 mg, 13%) as an off-white solid. deltaH (DMSOd6) 8.37-8.28 (IH, m), 8.20 (IH, d, J7.3 Hz), 8.13 (IH5 s), 8.06-7.97 (IH, m), 7.90-7.77 (2H, m), 7.44-7.36 (IH, m), 7.05-6.80 (2H, m), 5.48-5.37 and 5.31-5.23 (IH, m), 4.82 (IH, d, J 17.3 Hz), 4.37 (IH, d, J 17.2 Hz), 4.23-3.82 (2H, m), 3.45-3.20 (2H, under H2O), 1.45-1.30 (3H, m). LCMS (ES+) 399 (M+H)+, RT 16.73 minutes (Method 6).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 75; 76

34
[ 1242180-25-1 ]
[ 7709-13-9 ]
[ 1242179-26-5 ]

Yield	Reaction Conditions	Operation in experiment
9%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 120℃; for 1h;Microwave irradiation;	EXAMPLE 18N- {( IS)-I - r8-Chloro-2-( pyrrolidin- 1 -vDalphauinolm-3 -yl] ethvU - [1.3.51triazine-2.4-diamine To a solution of Intermediate 38 (44 mg, 0.16 mmol) in 1,4-dioxane (2 mL) were added 2-amino-4-chloro-[l,3,5]triazine (42 mg, 0.32 mmol) and DIPEA (0.06 mL, 0.35 mmol) and the mixture was heated at 12O0C under microwave irradiation for 1 h. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford the title compound (5.4 mg, 9%) as an off-white solid. deltaH (DMSOd6) 8.14-8.00 (IH, m), 7.74-7.62 (2H, m), 7.24-7.14 (IH, m), 6.83-6.73 (2H, m), 5.71-5.61 (IH, m), 3.78 (4H, d, J 17.65 Hz)5 2.52 (2H5 under DMSO)5 2.06-1.94 (4H, s), 1.40-1.33 (3H5 m). LCMS (ES+) 370 (MH-H)+, RT 3.42 minutes {Method 1).

Reference： [1]Patent: WO2010/100405,2010,A1 .Location in patent: Page/Page column 77; 78

35
[ 1548942-78-4 ]
[ 7709-13-9 ]
(S)-2-(1-(4-amino-1,3,5-triazin-2-yl)pyrrolidin-2-yl)-5-chloro-3-phenylpyrrolo[1,2-f][1,2,4]triazin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In butan-1-ol; for 1.5h;Reflux;	General procedure: A mixture of 1e (30 mg, 0.095 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (22 mg, 0.128 mmol) and TEA (0.05 ml, 0.360 mmol) in n-BuOH (3 mL) was stirred at reflux for 1.5 h. The reaction mixture was concentrated and purified by flash column chromatography eluting with MeOH/DCM to afford Compound 1 as a white solid (29 mg, yield: 64%). 2,4-dichloro-l,3,5-triazine(45 mg, 0.3 mmol) was added to 2 mL of NuEta320 aq., the reaction was stirred at -20 C for 10 min, then filtered, washed with water and dried to give 4-chloro- l,3,5-triazin-2-amine (18 mg, yield: 46%) as a yellow solid which was used in the next step without further purification. MS (m/z): 131.0 (M+H)+. (S)-2-(1-(4-amino- l,3,5-triazin-2-yl)pyrrolidin-2-yl)-5-chloro-3-phenylpyrrolo[1,2- f][1,2,4]triazin-4(3H)-one was prepared with <strong>[7709-13-9]4-chloro-1,3,5-triazin-2-amine</strong> as the material according to the procedure of Example 1 from le to Compound 1. MS (m/z): 409.1 (M+H)+. 1H NMR (400 MHz, CD3OD) delta: 8.02 (d, J= 1.6 Hz, 1H), 7.81 (d, J= 7.6 Hz, 1H), 7.64-7.54 (m, 3H), 7.42-7.39( m, 1H), 7.37-7.35 (m, 1H), 6.50-6.49 (m, 1H), 4.67-4.64 (m, 1H), 3.81-3.73 (m, 1H), 3.59-3.53 (m, 1H), 2.20-2.08 (m, 2H), 1.97 - 1.85 (m, 2H).
	With triethylamine; In butan-1-ol; for 1.5h;Reflux;	General procedure: A mixture of 1e (30 mg, 0.095 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (22 mg, 0.128 mmol) and TEA (0.05 ml, 0.360 mmol) in n-BuOH (3 mL) was stirred at reflux for 1.5 h. The reaction mixture was concentrated and purified by flash column chromatography eluting with MeOH/DCM to afford Compound 1 as a white solid (29 mg, yield: 64%). 2,4-dichloro-l,3,5-triazine(45 mg, 0.3 mmol) was added to 2 mL of NuEta320 aq., the reaction was stirred at -20 C for 10 min, then filtered, washed with water and dried to give 4-chloro- l,3,5-triazin-2-amine (18 mg, yield: 46%) as a yellow solid which was used in the next step without further purification. MS (m/z): 131.0 (M+H)+. (S)-2-(1-(4-amino- l,3,5-triazin-2-yl)pyrrolidin-2-yl)-5-chloro-3-phenylpyrrolo[1,2- f][1,2,4]triazin-4(3H)-one was prepared with <strong>[7709-13-9]4-chloro-1,3,5-triazin-2-amine</strong> as the material according to the procedure of Example 1 from le to Compound 1. MS (m/z): 409.1 (M+H)+. 1H NMR (400 MHz, CD3OD) delta: 8.02 (d, J= 1.6 Hz, 1H), 7.81 (d, J= 7.6 Hz, 1H), 7.64-7.54 (m, 3H), 7.42-7.39( m, 1H), 7.37-7.35 (m, 1H), 6.50-6.49 (m, 1H), 4.67-4.64 (m, 1H), 3.81-3.73 (m, 1H), 3.59-3.53 (m, 1H), 2.20-2.08 (m, 2H), 1.97 - 1.85 (m, 2H).

Reference： [1]Patent: WO2014/15523,2014,A1 .Location in patent: Page/Page column 38; 126; 127
[2]Patent: WO2014/15830,2014,A1 .Location in patent: Page/Page column 151

36
[ 67-56-1 ]
[ 124-41-4 ]
[ 7709-13-9 ]
[ 1122-73-2 ]

Yield	Reaction Conditions	Operation in experiment
1 g	at 0 - 20℃; for 1h;	To the solution of 4-chloro-1, 3, 5-triazin-2-amine (5.7 g, 44.0 mmol) in MeOH (100 mL) cooled to 0 was added CH3ONa (35.2 mL, 176.1 mmol, 5.0 M) dropwise. Then the mixture was stirred at room temperature for 1h. Half of the solvent was removed by vacuum, and the precipitate was filtered, washed with water to afford 4-methoxy-1, 3, 5-triazin-2-amine as a white solid (1.0 g) . LC-MS: m/z 127.1 (M+H) +.

Reference： [1]Patent: WO2018/39972,2018,A1 .Location in patent: Page/Page column 180-181

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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 7709-13-9 ] {[proInfo.proName]}

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[ 7709-13-9 ] Synthesis Path-Upstream 1~3

[ 7709-13-9 ] Synthesis Path-Downstream 1~36

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