[ CAS No. 273-70-1 ] {[proInfo.proName]}

Name: 273-70-1|Thiazolo[5,4-c]pyridine|97%
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Quality Control of [ 273-70-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 273-70-1 ]

Product Details of [ 273-70-1 ]

CAS No. :	273-70-1	MDL No. :	MFCD13179629
Formula :	C₆H₄N₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FHIMYVFGWKCROK-UHFFFAOYSA-N
M.W :	136.17	Pubchem ID :	14666228
Synonyms :

Calculated chemistry of [ 273-70-1 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	37.42
TPSA :	54.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.48
Log Po/w (XLOGP3) :	1.31
Log Po/w (WLOGP) :	1.69
Log Po/w (MLOGP) :	0.22
Log Po/w (SILICOS-IT) :	2.79
Consensus Log Po/w :	1.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.25
Solubility :	0.767 mg/ml ; 0.00563 mol/l
Class :	Soluble
Log S (Ali) :	-2.05
Solubility :	1.23 mg/ml ; 0.00902 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.57
Solubility :	0.37 mg/ml ; 0.00272 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.06

Safety of [ 273-70-1 ]

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 [ 273-70-1 ]

* 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 [ 273-70-1 ]
Downstream synthetic route of [ 273-70-1 ]

[ 273-70-1 ] Synthesis Path-Upstream 1~13

1
[ 365996-04-9 ]
[ 273-70-1 ]

Reference： [1] Heterocycles, 2004, vol. 63, # 7, p. 1555 - 1561
[2] Patent: EP1270557, 2003, A1,
[3] Patent: US2005/20645, 2005, A1,
[4] Patent: EP1577302, 2005, A1, . Location in patent: Page/Page column 67-68

2
[ 64-18-6 ]
[ 365996-04-9 ]
[ 273-70-1 ]

Reference： [1] Patent: EP1577301, 2005, A1, . Location in patent: Page/Page column 70-71
[2] Patent: EP1405852, 2004, A1, . Location in patent: Page 63-64

3
[ 98400-69-2 ]
[ 273-70-1 ]

Reference： [1] Heterocycles, 2004, vol. 63, # 7, p. 1555 - 1561

4
[ 98383-10-9 ]
[ 273-70-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 563 - 566

5
[ 129333-21-7 ]
[ 273-70-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 563 - 566

6
[ 129333-22-8 ]
[ 273-70-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 563 - 566

7
[ 129333-20-6 ]
[ 273-70-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 563 - 566

8
[ 70298-89-4 ]
[ 273-70-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 563 - 566

9
[ 52334-54-0 ]
[ 273-70-1 ]

Reference： [1] Pharmaceutical Bulletin, 1956, vol. 4, p. 216,219

10
[ 100724-20-7 ]
[ 273-70-1 ]

Reference： [1] Pharmaceutical Bulletin, 1956, vol. 4, p. 216,219

11
[ 52334-54-0 ]
[ 64-18-6 ]
[ 273-70-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 563 - 566

12
[ 273-70-1 ]
[ 74-88-4 ]
[ 259809-24-0 ]

Reference： [1] Patent: EP1577301, 2005, A1, . Location in patent: Page/Page column 71
[2] Patent: EP1270557, 2003, A1,
[3] Patent: US2005/20645, 2005, A1,
[4] Patent: EP1577302, 2005, A1, . Location in patent: Page/Page column 68

13
[ 273-70-1 ]
[ 259809-24-0 ]

Reference： [1] Heterocycles, 2004, vol. 63, # 7, p. 1555 - 1561

[ 273-70-1 ] Synthesis Path-Downstream 1~49

1
[ 52334-54-0 ]
[ 273-70-1 ]

Reference： [1]Pharmaceutical Bulletin,1956,vol. 4,p. 216,219

2
[ 52334-54-0 ]
[ 64-18-6 ]
[ 273-70-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 563 - 566

3
[ 52334-54-0 ]
[ 64-18-6 ]
zinc-powder [ No CAS ]
[ 273-70-1 ]

Reference： [1]Pharmaceutical Bulletin,1956,vol. 4,p. 216,219

4
[ 273-70-1 ]
[ 74-88-4 ]
5-methyl-thiazolo[5,4-<i>c</i>]pyridin-5-ium; iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In DMF (N,N-dimethyl-formamide); at 80℃; for 4h;	[Referential Example 4] 5-Methyl-4,5,6,7-tetrahydro<strong>[273-70-1]thiazolo[5,4-c]pyridine</strong>: The compound (1.61 g) obtained in Referential Example 3 was dissolved in N,N-dimethylformamide (50 ml), and to the solution methyl iodide (1.50 ml) was added, the resultant mixture was stirred at 80C for 4 hours.. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (100 ml), sodium borohydride (1.53 g) was added, and the resultant mixture was stirred at room temperature for 1 hour.. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of potassium carbonate and diethyl ether were added to the residue to separate an organic layer.. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.. The residue was purified by column chromatography on silica gel (methylene chloride:methanol = 25:1) to obtain the title compound (1.28 g).1H-NMR (CDCl3) delta: 2.52(3H,s), 2.83(2H,t,J=5.9Hz), 2.98(2H,t,J=5.9Hz), 3.70(2H,s), 8.63(1H,s). MS (FAB) m/z: 155(M+H)+.

Reference： [1]Heterocycles,2004,vol. 63,p. 1555 - 1561
[2]Patent: EP1405852,2004,A1 .Location in patent: Page 64

5
[ 365996-04-9 ]
[ 273-70-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In formic acid;	[Referential Example 3] Thiazolo[5,4-c]pyridine: 4-[(tert-Butoxycarbonyl)amino]-3-mercaptopyridine (33.2 g) was dissolved in formic acid (250 ml), and the solution was heated under reflux for 3 days. The reaction mixture was concentrated under reduced pressure, and a 5N aqueous solution (100 ml) of potassium hydroxide and ether were added to the residue to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate, and the solvent was thendistilled off under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol = 25:1) to obtain the title compound (9.03 g) as a colorless solid. 1H-NMR (CDCl3) delta: 8.05(1H,d,J=5.4Hz),8.70(1H,d,J=5.4Hz), 9.23(1H,s), 9.34(1H,s). MS (FAB) m/z: 137(M+H)+.
	With potassium hydroxide; In formic acid; diethyl ether;	REFERENTIAL EXAMPLE 3 Thiazolo[5,4-c]pyridine The compound (33.2 g) obtained in Referential Example 2 was dissolved in formic acid (250 ml), and the solution was heated under reflux for 3 days. The reaction mixture was concentrated under reduced pressure, and a 5N aqueous solution (100 ml) of potassium hydroxide and diethyl ether were added to the residue to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (methylene chloride:methanol=25:1) to obtain the title compound (9.03 g). 1H-NMR (CDCl3) delta: 8.05(1H,d,J=5.4 Hz), 8.70(1H,d,J=5.4 Hz), 9.23(1H,s), 9.34(1H,s). MS (FAB) m/z: 137(M+H)+.
	With formic acid; for 72h;Heating / reflux;	The compound (33.2 g) obtained in Referential Example 25 was dissolved in formic acid (250 ml) and the resulting mixture was heated under reflux for 3 days. The reaction mixture was concentrated under reduced pressure. A 5N aqueous solution (100 ml) of potassium hydroxide and diethyl ether were added to the residue to separate the layers. The organic layer was dried over anhydrous sodium sulfate and then, the solvent was distilled off under reduced pressure. The residue was purified by chromatography (methylene chloride:methanol = 25:1) on a silica gel column, whereby the title compound (9.03 g) was obtained.1H-NMR (CDCl3) delta : 8.05 (1H, d, J=5.4Hz), 8.70 (1H, d, J=5.4Hz), 9.23(1H,s), 9.34 (1H,s) . MS(FAB)m/z: 137(M+H)+.

Reference： [1]Heterocycles,2004,vol. 63,p. 1555 - 1561
[2]Patent: EP1270557,2003,A1
[3]Patent: US2005/20645,2005,A1
[4]Patent: EP1577302,2005,A1 .Location in patent: Page/Page column 67-68

6
[ 124-38-9 ]
[ 273-70-1 ]
lithium thiazolo[5,4-c]pyridin-2-carboxylate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5579 - 5586
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 1309 - 1330

7
[ 273-70-1 ]
1-[(5-Chloroindol-2-yl)sulfonyl]-4-[(thiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 1309 - 1330

8
[ 273-70-1 ]
[ 783289-80-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5579 - 5586

9
[ 273-70-1 ]
[4-(6-chloro-naphthalene-2-sulfonyl)-piperazin-1-yl]-(5-oxy-thiazolo[5,4-<i>c</i>]pyridin-2-yl)-methanone [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5579 - 5586

10
[ 273-70-1 ]
[ 259809-24-0 ]

Reference： [1]Heterocycles,2004,vol. 63,p. 1555 - 1561

11
[ 273-70-1 ]
6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid lithium salt [ No CAS ]

Reference： [1]Heterocycles,2004,vol. 63,p. 1555 - 1561

12
[ 98400-69-2 ]
[ 273-70-1 ]

Reference： [1]Heterocycles,2004,vol. 63,p. 1555 - 1561

13
[ 98383-10-9 ]
[ 273-70-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 563 - 566

14
[ 129333-21-7 ]
[ 273-70-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 563 - 566

15
[ 129333-22-8 ]
[ 273-70-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 563 - 566

16
[ 129333-20-6 ]
[ 273-70-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 563 - 566

17
[ 70298-89-4 ]
[ 273-70-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 563 - 566

18
[ 100724-20-7 ]
[ 273-70-1 ]

Reference： [1]Pharmaceutical Bulletin,1956,vol. 4,p. 216,219

19
[ 64-18-6 ]
[ 365996-04-9 ]
[ 273-70-1 ]

Yield	Reaction Conditions	Operation in experiment
	for 72h;Heating / reflux;	The compound obtained in Referential Example 2 (33.2 g) was dissolved in formic acid (250 mL), and the solution was heated under reflux for 3 days. The reaction mixture was concentrated under reduced pressure, and to the residue were added 5N aqueous potassium hydroxide (100 mL) and diethyl ether to partition the residue. The organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride : methanol = 25:1), to thereby give the title compound (9.03 g).1H-NMR(CDCl3) delta:8.05(1H, d, J=5.4Hz), 8.70(1H, d, J=5.4Hz), 9.23(1H, s), 9.34(1H, s). MS(FAB)m/z:137(M+H)+.
	for 72h;Heating / reflux;	[Referential Example 3] thiazolo[5,4-c]pyridine: The compound (33.2 g) obtained in Referential Example 2 was dissolved in formic acid (250 ml), and the solution was heated under reflux for 3 days.. The reaction mixture was concentrated under reduced pressure, and a 5N aqueous solution (100 ml) of potassium hydroxide and diethyl ether were added to the residue to separate an organic layer.. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure.. The residue was purified by column chromatography on silica gel (methylene chloride:methanol = 25:1) to obtain the title compound (9.03 g).1H-NMR (CDCl3) delta: 8.05(1H,d,J=5.4Hz), 8.70(1H,d,J=5.4Hz), 9.23(1H,s), 9.34(1H,s). MS (FAB) m/z: 137(M+H)+.

Reference： [1]Patent: EP1577301,2005,A1 .Location in patent: Page/Page column 70-71
[2]Patent: EP1405852,2004,A1 .Location in patent: Page 63-64

20
[ 273-70-1 ]
[ 74-88-4 ]
[ 259809-24-0 ]

Yield	Reaction Conditions	Operation in experiment
		The compound obtained in Referential Example 3(1.61 g) was dissolved in N, N-dimethylformamide (50 mL), and methyl iodide (1.50 mL) was added thereto, followed by stirring at 80C for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (100 mL), and sodium borohydride (1.53 g) was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and to the residue were added saturated aqueous potassium carbonate and diethyl ether to partition the residue. The organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride : methanol = 25:1), to thereby give the title compound (1.28 g).1H-NMR(CDCl3) delta:2.52(3H, s), 2.83(2H, t, J=5.9Hz), 2.98(2H, t, J=5.9Hz), 3.70(2H, s), 8.63(1H, s). MS(FAB)m/z:155(M+H)+.
	With sodium borohydrid; potassium carbonate; In methanol; N,N-dimethyl-formamide;	[Referential Example 4] 5-Methyl-4,5,6,7-tetrahydro<strong>[273-70-1]thiazolo[5,4-c]pyridine</strong>: Thiazolo[5,4-c]pyridine (1.61 g) was dissolved in N,N-dimethylformamide (50 ml), and to the solution methyl iodide (1.50 ml) was added, the resultant mixture was stirred at 80C for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (100 ml), sodium borohydride (1.53 g) was added, and the resultant mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of potassium carbonate and ether were added to the residue to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol = 25:1) to obtain the title compound (1.28 g) as a paleyellow oil. 1H-NMR (CDCl3) delta: 2.52(3H,s), 2.83(2H,t,J=5.9Hz), 2.98(2H,t,J=5.9Hz),3.70(2H,s), 8.63(1H,s). MS (FAB) m/z: 155(M+H)+.
	With sodium borohydrid; potassium carbonate; In methanol; diethyl ether; N,N-dimethyl-formamide;	REFERENTIAL EXAMPLE 4 5-Methyl-4,5,6,7-tetrahydro<strong>[273-70-1]thiazolo[5,4-c]pyridine</strong>: The compound (1.61 g) obtained in Referential Example 3 was dissolved in N,N-dimethylformamide (50 ml), and to the solution methyl iodide (1.50 ml) was added, the resultant mixture was stirred at 80 C. for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (100 ml), sodium borohydride (1.53 g) was added, and the resultant mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of potassium carbonate and diethyl ether were added to the residue to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (methylene chloride:methanol=25:1) to obtain the title compound (1.28 g). 1H-NMR (CDCl3) delta: 2.52(3H,s), 2.83(2H,t,J=5.9 Hz), 2.98(2H,t,J=5.9 Hz), 3.70(2H,s), 8.63(1H,s). MS (FAB) m/z: 155(M+H)+.

The compound (1.61 g) obtained in Referential Example 26 was dissolved in N,N-dimethylformamide (50 ml). After addition of methyl iodide (1.50 ml), the resulting mixture was stirred under heat at 80C for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (100 ml). Sodium borohydride (1.53 g) was added to the resulting solution and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. A saturated aqueous solution of potassium carbonate and diethyl ether were added to the residue to separate the layers. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by chromatography (methylene chloride:methanol = 25:1) on a silica gel column, whereby the title compound (1.28 g) was obtained.1H-NMR (CDCl3)delta: 2.52 (3H, s), 2.83(2H,t,J=5.9Hz), 2.98 (2H, t, J=5.9Hz), 3.70 (2H, s), 8.63(1H, s). MS (FAB)m/z: 155(M+H)+.

Reference： [1]Patent: EP1577301,2005,A1 .Location in patent: Page/Page column 71
[2]Patent: EP1270557,2003,A1
[3]Patent: US2005/20645,2005,A1
[4]Patent: EP1577302,2005,A1 .Location in patent: Page/Page column 68

21
[ 273-70-1 ]
[ 76-02-8 ]
C₈H₃Cl₃N₂OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6396 - 6400

22
[ 273-70-1 ]
C₈H₄N₄O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6396 - 6400

23
[ 273-70-1 ]
C₁₅H₁₁N₅OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6396 - 6400

24
[ 273-70-1 ]
C₇H₆N₄OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6396 - 6400

25
[ 273-70-1 ]
2-cyclohex-1-enylthiazolo[5,4-c]pyridine [ No CAS ]