[ CAS No. 17467-35-5 ] {[proInfo.proName]}

Name: 17467-35-5|5-Amino-3-methyl-1,2,4-thiadiazole|98%
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SKU: A182705
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2D 3D

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Quality Control of [ 17467-35-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17467-35-5 ]

SDS Specification

Alternatived Products of [ 17467-35-5 ]

Product Details of [ 17467-35-5 ]

CAS No. :	17467-35-5	MDL No. :	MFCD01114751
Formula :	C₃H₅N₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DJKUIGPCSNRFRK-UHFFFAOYSA-N
M.W :	115.16	Pubchem ID :	350639
Synonyms :

Calculated chemistry of [ 17467-35-5 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	29.28
TPSA :	80.04 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) :	-6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.09
Log Po/w (XLOGP3) :	0.89
Log Po/w (WLOGP) :	0.44
Log Po/w (MLOGP) :	-1.13
Log Po/w (SILICOS-IT) :	1.62
Consensus Log Po/w :	0.58

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.64
Solubility :	2.62 mg/ml ; 0.0227 mol/l
Class :	Very soluble
Log S (Ali) :	-2.16
Solubility :	0.805 mg/ml ; 0.00699 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.89
Solubility :	14.7 mg/ml ; 0.128 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.29

Safety of [ 17467-35-5 ]

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

Application In Synthesis of [ 17467-35-5 ]

* 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 [ 17467-35-5 ]
Downstream synthetic route of [ 17467-35-5 ]

[ 17467-35-5 ] Synthesis Path-Upstream 1~7

1
[ 17467-35-5 ]
[ 54681-68-4 ]

Reference： [1] Chemische Berichte, 1956, vol. 89, p. 1534,1540

2
[ 333-20-0 ]
[ 20846-52-0 ]
[ 17467-35-5 ]

Yield	Reaction Conditions	Operation in experiment
32%	at 0 - 20℃; for 12 h;	Compound LXII (5.1 g, 55 mmol) was dissolved in methanol (250 mL) and the resulting solution was cooled to 0° C. Potassium thiocyanate (5.3 g, 55 mmol) was then added. The resulting solution was stirred for 12 hours at room temperature, concentrated under reduced pressure, diluted with ethyl acetate (200 mL), and filtered under reduced pressure to remove a solid. The filtrate was concentrated under reduced pressure, creating a solid which was filtered under reduced pressure to yield Compound LXIII (2 g (32percent)). The filtrate was further concentrated and applied to column chromatography (SiO2, n-hex:EA=4:1) to yield Compound LXIII (2 g (32percent)).¹H NMR (600 MHz, CD₃OD) δ 3.27 (s, 3H)
32%	at 0 - 20℃; for 12 h;	Compound LXII (5,1 g, 55 mmol) was dissolved in methanol (250 mL) and the resulting solution was cooled to 0 . Potassium thiocyanate (5.3 g, 55 mmol) was then added. The resulting solution was stirred for 12 hours at room temperature, concentrated under reduced pressure, diluted with ethyl acetate (200 mL), and filtered under reduced pressure to remove a solid. The filtrate was concentrated under reduced pressure, creating a solid which was filtered under reduced pressure to yield Compound LXIII (2 g (32percent)). The filtrate was further concentrated and applied to column chromatography (SiO2, n-hex : EA = 4 : 1) to yield Compound LXIII (2 g (32percent)). ¹H NMR (600MHz, CD₃OD) δ 3.27(s, 3H)

Reference： [1] Patent: US2012/264727, 2012, A1, . Location in patent: Page/Page column 53
[2] Patent: EP2706062, 2014, A2, . Location in patent: Paragraph 0199

3
[ 118493-85-9 ]
[ 17467-35-5 ]

Reference： [1] Patent: US5773624, 1998, A,

4
[ 124-42-5 ]
[ 333-20-0 ]
[ 17467-35-5 ]

Reference： [1] Gazzetta Chimica Italiana, 1977, vol. 107, p. 1 - 5
[2] Bioorganic and medicinal chemistry, 2001, vol. 9, # 12, p. 3231 - 3241

5
[ 21734-85-0 ]
[ 17467-35-5 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1971, vol. 36, p. 4091 - 4098

6
[ 124-42-5 ]
[ 17467-35-5 ]

Reference： [1] Chemische Berichte, 1954, vol. 87, p. 68,74[2] Chemische Berichte, 1956, vol. 89, p. 1534,1540

7
[ 67-56-1 ]
[ 7726-95-6 ]
[ 124-41-4 ]
[ 143-37-3 ]
[ 17467-35-5 ]

Reference： [1] Chemische Berichte, 1954, vol. 87, p. 68,74[2] Chemische Berichte, 1956, vol. 89, p. 1534,1540

[ 17467-35-5 ] Synthesis Path-Downstream 1~7

1
[ 17467-35-5 ]
[ 54681-68-4 ]

Reference： [1]Chemische Berichte,1956,vol. 89,p. 1534,1540

2
[ 21734-85-0 ]
[ 17467-35-5 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1971,vol. 36,p. 4091 - 4098

3
[ 17467-35-5 ]
[ 98349-24-7 ]
[ 122-51-0 ]
ethyl 6,7-difluoro-1-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; In ethanol; chloroform; N,N-dimethyl-formamide;	EXAMPLE 34 Ethyl 6,7-difluoro-1-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylate (Compound No.73) A mixture of <strong>[98349-24-7]ethyl 2,4,5-trifluorobenzoylacetate</strong> (3.7 g), ethyl orthoformate (3.9 ml) and acetic anhydride (4.3 ml) was stirred at 135 C. for 3 hours. After the solvent was removed in vacuo, the residue was added with chloroform (20 ml) and ethanol (10 ml). 3-Methyl-5-amino-1,2,4-thiadiazole (1.73 g) was added thereto for allowing to react for 15 hours at the same temperature. The solvent was removed. The residue was purified by chromatography on silicagel(chloroform/ethyl acetate 1:1 as an eluent). An yellow oil (4.9 g) was obtained. To a solution of this oily compound (4.5 g) in N,N-dimethylformamide (60 ml), 490 mg of sodium hydride (60% in oil) was added. Then the solution was stirred for 5 minutes at 100 C. The solvent was removed. The residue was added with chloroform and water, for extracting an organic layer, followed by evaporation. The precipitated solid was collected and washed with ethanol, ether and n-hexane, successively. The title compound No. 73 was obtained as a pale brown solid (2.4 g). Melting point: 157-159 C. 1 H-NMR(CDCl3) delta; 1.42(t,J=7 Hz,3H), 2.78(s,3H), 4.43(q,J=7 Hz,2H), 8.17-8.32(m,2H), 8.77(s,1H)

Reference： [1]Patent: US5412098,1995,A

4
[ 17467-35-5 ]
[ 1702-17-6 ]
[ 1018966-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20 - 50℃; for 1h;	Step 1 Production of 3,6-dichloro-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridine-2-carboxamide 12 g of 5-amino-3-methyl-1,2,4-thiadiazole, 21.1 g of N-hydroxybenzotriazole hydrate and 29.8 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added to a chloroform (500 ml) solution of 21 g of <strong>[1702-17-6]3,6-dichloro-2-pyridinecarboxylic acid</strong>, and stirred at room temperature for 1 hour and then stirred overnight at 50 C. The reaction liquid was diluted with chloroform, then washed with aqueous 0.2 N hydrochloric acid solution, water and saturated saline water. After this was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and ethyl acetate was added to the resulting residue for crystallization to obtain 22.7 g of the entitled compound as a white solid.

Reference： [1]Patent: US2008/90799,2008,A1 .Location in patent: Page/Page column 16

5
[ 17467-35-5 ]
[ 394-02-5 ]
C₁₀H₇FN₄O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1357 - 1360

6
[ 21734-85-0 ]
[ 17467-35-5 ]
3-methyl-N-(3-methyl-1,2,4-thiadiazol-5-yl)-1,2,4-thiadiazol-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
700 mg		NaH (60% in oil) (50mg) was added to a solution of 3-methyl-1,2,4-thiadiazol-5- amine (1) (115mg, immol) in NMP (2mL). After 10mm, 5-chloro-3-methyl-1,2,4- thiadiazole (2) (140mg, 1.O5mmol) was added and the resultant mixture stirred at45C under N2(g). After 4h, the reaction mixture was diluted with EtOAc and extracted with saturated bicarbonate solution (x3). Analysis indicated that all desired product was in the aqueous phase. The combined aqueous phases were concentrated to dryness; the resultant residue was slurried with MeCN (2 x 100mL) and filtered. The filtrate was concentrated to afford (3) as an oil I NMP solution(700mg).LCMS (ES): found 214.0 [M+H].
700 mg		NaH (60% in oil) (50mg) was added to a solution of 3-methyl-1 ,2,4-thiadiazol-5 amine (1 ) (1 15mg, 1 mmol) in NMP (2ml_). After 10min, 5-chloro-3-methyl-1 ,2,4 thiadiazole (2) (140mg, 1 .05mmol) was added and the resultant mixture stirred at 45C under N2(g). After 4h, the reaction mixture was diluted with EtOAc and extracted with saturated bicarbonate solution (x3). Analysis indicated that all desired product was in the aqueous phase. The combined aqueous phases were concentrated to dryness; the resultant residue was slurried with MeCN (2 x 100ml_) and filtered. The filtrate was concentrated to afford (3) as an oil / NMP solution (700mg). LCMS (ES): found 214.0 [M+H]+.
700 mg		Example B (0205) 4-[Bis(3-methyl-1 ,2,4-thiadiazol-5-yl)amino]methyl}-2-fluoro-N- (0206) (0207) (0208) 4 (0209) (0210) NaH (60% in oil) (50mg) was added to a solution of 3-methyl-1 ,2,4-thiadiazol-5- amine (1) (1 15mg, 1 mmol) in NMP (2ml_). After 10min, 5-chloro-3-methyl-1 ,2,4- thiadiazole (2) (140mg, 1.05mmol) was added and the resultant mixture stirred at 45C under N2(g). After 4h, the reaction mixture was diluted with EtOAc and extracted with saturated bicarbonate solution (x3). Analysis indicated that all desired product was in the aqueous phase. The combined aqueous phases were concentrated to dryness; the resultant residue was slurried with MeCN (2 x 100ml_) and filtered. The filtrate was concentrated to afford (3) as an oil / NMP solution (700mg). (0211) LCMS (ES): found 214.0 [M+H]+.

Reference： [1]Patent: WO2014/181137,2014,A1 .Location in patent: Page/Page column 24
[2]Patent: WO2017/29514,2017,A1 .Location in patent: Page/Page column 49; 50
[3]Patent: WO2017/208032,2017,A1 .Location in patent: Page/Page column 29-30

7
[ 220227-21-4 ]
[ 17467-35-5 ]
2,4,5-trifluoro-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzene-1-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 40℃; for 16h;	41.1 Synthesis of 2,4,5-trifluoro-N-(3-methyl-1 ,2,4-thiadiazol-5-yl)benzene-1 -sulfonamide Into a 100-mL 3-necked round-bottom flask, were placed 3-methyl-1 ,2,4-thiadiazol-5-amine (2 g, 17.37 mmol, 1 .00 equiv), MeCN (50 mL), DBU (3.9 g, 25.62 mmol, 1 .50 equiv), 2,4,5-trifluorobenzene-1 - sulfonyl chloride (6 g, 26.02mmol, 1 .50 equiv). The resulting solution was stirred for 16 h at 40°C. The resulting mixture was concentrated under vacuum . The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :8). This resulted in 1 .5 g (28%) of 2,4,5-trifluoro-N-(3-methyl-1 ,2,4- thiadiazol-5-yl)benzene-1 -sulfonamide as yellow oil.

Reference： [1]Current Patent Assignee: DEGIACOMO; DEGIACOMO MARK G - WO2015/130957, 2015, A1 Location in patent: Page/Page column 104

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Ghs Precautionary Statements

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P320
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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. 17467-35-5 ] {[proInfo.proName]}

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[ 17467-35-5 ] Synthesis Path-Upstream 1~7

[ 17467-35-5 ] Synthesis Path-Downstream 1~7

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Amines

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Thiadiazoles

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