[ CAS No. 315702-99-9 ] {[proInfo.proName]}

Name: 315702-99-9|4-(Pyridin-4-yl)-N-(m-tolyl)thiazol-2-amine|95%
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SKU: A134944
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Quality Control of [ 315702-99-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 315702-99-9 ]

CAS No. :	315702-99-9	MDL No. :	MFCD01121974
Formula :	C₁₅H₁₃N₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KATNUHQNJGNLPW-UHFFFAOYSA-N
M.W :	267.35	Pubchem ID :	704473
Synonyms :		Chemical Name :	4-(Pyridin-4-yl)-N-(m-tolyl)thiazol-2-amine

Calculated chemistry of [ 315702-99-9 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	17
Fraction Csp3 :	0.07
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	79.85
TPSA :	66.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.56
Log Po/w (XLOGP3) :	3.78
Log Po/w (WLOGP) :	4.26
Log Po/w (MLOGP) :	2.14
Log Po/w (SILICOS-IT) :	4.34
Consensus Log Po/w :	3.42

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.34
Solubility :	0.0121 mg/ml ; 0.0000454 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.86
Solubility :	0.00368 mg/ml ; 0.0000138 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.4
Solubility :	0.000107 mg/ml ; 0.000000402 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.59

Safety of [ 315702-99-9 ]

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

Application In Synthesis of [ 315702-99-9 ]

* 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 [ 315702-99-9 ]
Downstream synthetic route of [ 315702-99-9 ]

[ 315702-99-9 ] Synthesis Path-Upstream 1~3

1
[ 621-40-9 ]
[ 5349-17-7 ]
[ 315702-99-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: for 3 h; Heating; Reflux Stage #2: With ammonia In ethanol; water at 20℃; for 2 h;	7V-(3-Methylphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (5) ("STF- 62247"). A mixture of bromoketone hydrobromide 1 (1.13 g, 4.03 mmol) and 3- methylphenylthiourea 4 (0.67 g, 4.03 mmol) in EtOH (20 mL) was stirred at reflux temperature for 3 h. The mixture was cooled to 20 ⁰C, diluted with water (50 mL), the pH adjusted to ca. 8 with aqueous NH₃ and the mixture stirred at 20 ⁰C for 2 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with a gradient (50-100percent) of EtO Ac/pet, ether, to give amine 5 (0.94 g, 87percent) as a cream powder: mp(EtOAc/pet. ether) 158-160 ⁰C; ¹H NMR δ 10.27 (br s, 1 H, NH), 8.62 (dd, J = 4.6, 1.6 Hz, 2 H, H-2', H-6'), 7.84 (dd, J= 4.6, 1.6 Hz, 2 H, H-3', H-5'), 7.69 (s, 1 <n="82"/>H, H-5), 7.57 (br d, J= 7.9 Hz, 1 H, H-6"), 7.47 (br s, 1 H, H-2"), 7.24 (dd, J= 7.8, 7.5 Hz, 1 H, H-5"), 6.81 (br d, J= 7.5 Hz, 1 H, H-4"), 2.33 (s, 3 H, CH₃); ¹³C NMR δ 163.5, 150.1 (2), 147.6, 140.9, 140.8, 138.1, 128.8, 122.2, 119.8 (2), 117.5, 114.1, 107.2, 21.2; MS m/z 268.4 (MH⁺, 100percent). Anal, calcd for Ci₅Hi₃N₃S-¹Z₄H₂O: C, 66.27; H, 5.01; N, 15.46. Found: C, 64.48; H, 5.08; N, 15.08percent.

Reference： [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 787 - 797
[2] Patent: WO2009/114552, 2009, A1, . Location in patent: Page/Page column 80-81

2
[ 1122-54-9 ]
[ 315702-99-9 ]

Reference： [1] Patent: WO2009/114552, 2009, A1,

3
[ 108-44-1 ]
[ 315702-99-9 ]

Reference： [1] Patent: WO2009/114552, 2009, A1,

[ 315702-99-9 ] Synthesis Path-Downstream 1~20

1
[ 315702-99-9 ]
[ 74-88-4 ]
[ 1187669-19-7 ]

Yield	Reaction Conditions	Operation in experiment
86%		Example 1-587V-Methyl-7V-(3-methylphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (95). [0311] 7V-Methyl-7V-(3-methylphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (95). NaH (216 mg, 5.4 mmol) was added to a stirred solution of amine 5 (760 mg, 2.8 mmol) in DMF (5 mL) and the mixture stirred at 20 0C for 2 min. MeI (0.18 mL, 2.8 mmol) was added dropwise and the mixture stirred at 20 0C for 1 h. The reaction was quenched with saturated aqueous NH4Cl solution (15 mL) and the mixture extracted with EtOAc (3 x 15 mL). The combined organic fraction was dried and the solvent evaporated. The crude solid was purified by column chromatography, eluting with a gradient (50-100percent) of EtO Ac/pet, ether, to give amine 95 (0.69 g, 86percent) as a colourless oil: 1H NMR (CDCl3) delta 8.60 (dd, J= 4.6, 1.5 Hz, 2 H, H-2', H-6'), 7.71 (dd, J= 4.6, 1.6 Hz, 2 H, H-3', H-5'), 7.33 (dd, J = 7.8, 7.6 Hz, 1 H, H-5"), 7.20-7.24 (m, 2 H, H-2", H-6"), 7.11 (br d, J= 7.6 Hz, 1 H, H-4"), 6.90 (s, 1 H, H-5), 3.60 (s, 3 H, NCH3), 2.39 (s, 3 H, CH3); 13C NMR (CDCl3) delta 170.1, 150.1 (2), 149.0, 146.1, 141.9, 139.9, 129.6, 127.5, 125.7, 122.1, <n="133"/>120.2 (2), 105.4, 40.4, 21.4; MS m/z 282.5 (MH+, 100percent). Anal, calcd for Ci6Hi5N3S: C, 68.30; H, 5.37; N, 14.93. Found: C, 67.97; H, 5.45; N, 14.86percent.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 131-132

2
[ 315702-99-9 ]
[ 75-03-6 ]
[ 1187669-20-0 ]

Yield	Reaction Conditions	Operation in experiment
93%		Example 1-59 7V-Ethyl-7V-(3-methylphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (96). [0312] 7V-Ethyl-7V-(3-methylphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (96).NaH (151 mg, 3.8 mmol) was added to a stirred solution of amine 5 (533 mg, 2.0 mmol) in DMF (8 mL) and the mixture stirred at 20 0C for 2 min. EtI (0.16 niL, 2.0 mmol) was added dropwise and the mixture stirred at 20 0C for 1 h. The reaction was quenched with saturated aqueous NH4Cl solution (10 mL) and the mixture extracted with EtOAc (3 x 15 mL). The combined organic fraction was dried and the solvent evaporated. The crude solid was purified by column chromatography, eluting with 50percent EtO Ac/pet, ether, to give amine 96 (0.55 g, 93percent) as a colourless oil: 1H NMR (CDCl3) delta 8.60 (dd, J= 4.6, 1.5 Hz, 2 H, H-T, H-6'), 7.71 (dd, J= 4.6, 1.6 Hz, 2 H, H-3\\ H-5'), 7.34 (br dd, J= 8.6, 7.4 Hz, 1 H, H-5"), 7.14-7.20 (m, 3 H, H-2", H-4", H-6"), 6.87 (s, 1 H, H-5), 4.08 (q, J= 7.1 Hz, 2 H, CH2N), 2.39 (s, 3 H, CH3), 1.32 (t, J= 7.1 Hz, 3 H, CH3); 13C NMR (CDCl3) delta 170.0, 150.1 (2), 149.0, 144.6, 142.0, 140.1, 129.8, 128.2, 127.6, 124.1, 120.2 (2), 105.0, 47.7, 21.4, 13.1; MS m/z 296.5 (MH+, 100percent). Anal, calcd for Ci7Hi7N3S: C, 69.12; H, 5.80; N, 14.22. Found: C, 68.90; H, 5.89; N, 14.28percent.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 132

3
[ 621-40-9 ]
[ 5349-17-7 ]
[ 315702-99-9 ]

Yield	Reaction Conditions	Operation in experiment
87%		7V-(3-Methylphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (5) ("STF- 62247"). A mixture of bromoketone hydrobromide 1 (1.13 g, 4.03 mmol) and 3- methylphenylthiourea 4 (0.67 g, 4.03 mmol) in EtOH (20 mL) was stirred at reflux temperature for 3 h. The mixture was cooled to 20 0C, diluted with water (50 mL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 20 0C for 2 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with a gradient (50-100percent) of EtO Ac/pet, ether, to give amine 5 (0.94 g, 87percent) as a cream powder: mp(EtOAc/pet. ether) 158-160 0C; 1H NMR delta 10.27 (br s, 1 H, NH), 8.62 (dd, J = 4.6, 1.6 Hz, 2 H, H-2', H-6'), 7.84 (dd, J= 4.6, 1.6 Hz, 2 H, H-3', H-5'), 7.69 (s, 1 <n="82"/>H, H-5), 7.57 (br d, J= 7.9 Hz, 1 H, H-6"), 7.47 (br s, 1 H, H-2"), 7.24 (dd, J= 7.8, 7.5 Hz, 1 H, H-5"), 6.81 (br d, J= 7.5 Hz, 1 H, H-4"), 2.33 (s, 3 H, CH3); 13C NMR delta 163.5, 150.1 (2), 147.6, 140.9, 140.8, 138.1, 128.8, 122.2, 119.8 (2), 117.5, 114.1, 107.2, 21.2; MS m/z 268.4 (MH+, 100percent). Anal, calcd for Ci5Hi3N3S-1Z4H2O: C, 66.27; H, 5.01; N, 15.46. Found: C, 64.48; H, 5.08; N, 15.08percent.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 80-81

4
[ 50-00-0 ]
[ 315702-99-9 ]
[ 1187668-87-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine; In tetrahydrofuran; water; at 130℃; for 1h;	Example 1-40 [2-[(3-Methylphenyl)amino]-4-(4-pyridinyl)-l,3-thiazol-5-yl]methanol (74). [0290] [2- [(3-Methylphenyl)amino] -4-(4-pyridinyl)- 1 ,3-thiazol-5-yl] methanol(74). A mixture of amine 5 (1.02 g, 1.87 mmol), 40percent aqueous formaldehyde solution (10 mL) and Et3N (3 mL) in THF (10 mL) was stirred in a glass pressure vessel at 130 0C for 1 h. The mixture was cooled to 20 0C, the reaction quenched with cNH3 solution (6 mL) and the mixture diluted with water (100 mL). The mixture was extracted with EtOAc (3 x 50 mL), the combined organic fraction was dried and the solvent evaporated. The crude solid was purified by column chromatography, eluting with a gradient (0-5percent) of MeOH/DCM, to give (i) starting material 5 (93 mg, 9percent) and (ii) alcohol 74 (874 mg, 77percent) as a white powder: mp (MeOH/DCM) 161-163 0C; 1U NMR delta 10.12 (br s, 1 H, NH), 8.64 (dd, J= 4.5, 1.6 Hz, 2 H, H-2", H-6"), 7.65 (dd, J= 4.5, 1.6 Hz, 2 H, H-3", H-5"), 7.52 (dd, J= 8.0, 1.8 Hz, 1 H, H-6'"), 7.40 (br s, 1 H, H-2'"), 7.21 (dd, J= 8.0, 7.5 Hz, 1 H, H-5'"), 6.79 (br d, J= 7.5 Hz, 1 H, H-4'"), 5.71 (t, J= 5.5 Hz, 1 H, OH), 4.70 (d, J= 5.5 Hz, 2 H, H-I), 2.30 (s, 3 H, CH3); 13C NMR delta 161.2, 149.8 (2), 142.7, 141.5, 140.9, 138.0, 128.7, 127.6, 122.1 (2), 122.0, 117.4, 114.1, 55.4, 21.2; <n="118"/>MS m/z 298.5 (MH+, 100percent). Anal, calcd for Ci6Hi5N3OS: C, 64.62; H, 5.08; N, 14.13. Found: C, 64.70; H, 5.18; N, 14.08percent.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 116-117

5
[ 624-76-0 ]
[ 315702-99-9 ]
[ 1187669-21-1 ]

Yield	Reaction Conditions	Operation in experiment
19%		Example 1-60 2-{3-Methyl[4-(4-pyridinyl)-l,3-thiazol-2-yl]anilino}ethanol (97). [0313] 2-{3-Methyl[4-(4-pyridinyl)-l,3-thiazol-2-yl]anilino}ethanol (97). NaH(107 mg, 2.7 mmol) was added to a stirred solution of amine 5 (649 mg, 2.4 mmol) in DMF (10 mL) and the mixture stirred at 20 0C for 2 min. Iodoethanol (0.19 mL, <n="134"/>2.4 mmol) was added dropwise and the mixture stirred at 20 0C for 48 h. The reaction was quenched with saturated aqueous NH4Cl solution (10 rnL) and the mixture extracted with EtOAc (3 x 15 mL). The combined organic fraction was dried and the solvent evaporated. The crude solid was purified by column chromatography, eluting with a gradient (50-100percent) of EtO Ac/pet, ether, to give (i) starting material 5 (0.22 g, 34percent) and (ii) amine 97 (0.15 g, 19percent) as a white powder: mp (EtOAc/pet. ether) 149-151 0C; 1H NMR delta 8.58 (dd, J= 4.5, 1.6 Hz, 2 H, H-2"', H-6"'), 7.78 (dd, J= 4.5, 1.6 Hz, 2 H, H-3"', H-5"'), 7.47 (s, 1 H, H-5"), 7.30-7.40 (m, 3 H, H-2', H-4', H-5'), 7.34 (br dd, J= 7.4 Hz, 1 H, H-6'), 4.80 (t, J = 5.5 Hz, 1 H, OH), 4.03 (t, J= 6.2 Hz, 2 H, H-2), 3.71 (dt, J= 6.2, 5.5 Hz, 2 H, H-I), 2.35 (s, 3 H, CH3); 13C NMR delta 169.4, 149.9 (2), 147.7, 144.8, 141.1, 139.4, 129.6, 127.9, 127.0, 123.6, 119.8 (2), 106.6, 57.7, 54.9, 20.8; MS m/z 312.6 (MH+, 100percent). Anal, calcd for Ci7Hi7N3OS: C, 65.57; H, 5.50; N, 13.49. Found: C, 65.87; H, 5.43; N, 13.65percent.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 132-133

6
[ 315702-99-9 ]
[ 1187669-65-3 ]

Yield	Reaction Conditions	Operation in experiment
45%		Example 1-105 JV-(3-Methylphenyl)-4-(l-oxido-4-pyridinyl)-l,3-thiazol-2-amine (188). [0397] 7V-(3-Methylphenyl)-4-(l-oxido-4-pyridinyl)-l,3-thiazol-2-amine (188). MCPBA (50-55percent, 710 mg, 2.1 mmol) was added to a solution of amine 5 (500 mg, 1.9 mmol) in DCM (30 mL) and the reaction mixture was stirred at 20 0C for 24 h. The mixture was diluted with DCM (50 mL), washed with sat. aq. NaHCO3 solution (50 mL), washed with sat. aq. Na2S2Os solution (50 mL), and washed with brine (50 mL). The solution was dried, the solvent was evaporated and the residue was purified by chromatography, eluting with 5percent DCM/MeOH, to give the TV- oxide 188 (240 mg, 45percent) as a yellow powder: mp (EtO Ac/pet. ether) 162-164 0C; 1H NMR delta 10.26 (s, 1 H, NH), 8.24 (dt, J= 7.2, 2.5 Hz, 2 H, H-2', H-6') 7.86 (dt, J = 7.2, 2.5 Hz, 2 H, H-3', H-5'), 7.58-7.56 (m, 2 H, H-5, H-6"), 7.44 (br s, 1 H, H- 2"), 7.23 (t, J= 7.7 Hz, 1 H, H-5"), 6.81 (d, J= 7.5 Hz, 1 H, H-4"), 2.32 (s, 3 H, CH3); 13C NMR delta 163.6, 146.6, 140.9, 138.8 (2), 138.2, 130.8, 128.9, 122.6 (2), <n="179"/>122.3, 117.6, 114.2, 106.1, 21.3; MS m/z 284.6 (MH+, 100percent). Anal, calcd for Ci5Hi3N3OS: C, 63.58; H, 4.62; N, 14.83. Found: C, 63.08; H, 4.59; N, 14.86percent.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 177-178

7
[ 1122-54-9 ]
[ 315702-99-9 ]