[ CAS No. 101080-15-3 ] {[proInfo.proName]}

Name: 101080-15-3|5-Isopropylthiazol-2-amine|97%
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Quality Control of [ 101080-15-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 101080-15-3 ]

SDS Specification

Alternatived Products of [ 101080-15-3 ]

Product Details of [ 101080-15-3 ]

CAS No. :	101080-15-3	MDL No. :	MFCD13185908
Formula :	C₆H₁₀N₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MENMPXBUKLPJKR-UHFFFAOYSA-N
M.W :	142.22	Pubchem ID :	10486954
Synonyms :

Calculated chemistry of [ 101080-15-3 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.1
TPSA :	67.15 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) :	-5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.67
Log Po/w (XLOGP3) :	1.77
Log Po/w (WLOGP) :	1.86
Log Po/w (MLOGP) :	0.59
Log Po/w (SILICOS-IT) :	2.21
Consensus Log Po/w :	1.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.18
Solubility :	0.935 mg/ml ; 0.00658 mol/l
Class :	Soluble
Log S (Ali) :	-2.8
Solubility :	0.226 mg/ml ; 0.00159 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.73
Solubility :	2.63 mg/ml ; 0.0185 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.39

Safety of [ 101080-15-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 101080-15-3 ]

* 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 [ 101080-15-3 ]
Downstream synthetic route of [ 101080-15-3 ]

[ 101080-15-3 ] Synthesis Path-Upstream 1~7

1
[ 17356-08-0 ]
[ 590-86-3 ]
[ 101080-15-3 ]

Yield	Reaction Conditions	Operation in experiment
42%	Stage #1: With bromine In 1,4-dioxane at 0 - 20℃; for 2 h; Stage #2: at 20℃; for 6 h;	2 ml (18.6 mmol) of 3-methylbutyraldehyde were dissolved in 15 ml of dioxane. 40.4 ml (18.6 mmol) of a solution 2 percent v/v of bromine in dioxane was dropped therein at 0°C. The mixture was maintained at room temperature under stirring for 2 hours, then 2.83 g (37.2 mmol) of thiourea and 5 ml of ethanol were added. After 6 hours at room temperature the solution was evaporated to dryness, the residue was dissolved in methylene chloride and the product extracted with 1M hydrochloric acid; the aqueous layer was made basic by using 30percent ammonium hydrate and extracted again with methylene chloride. The organic phase was dried over sodium sulfate and evaporated under vacuum. The residue was chromatographed on a silica gel column, eluting with cyclohexane-ethylacetate to give 1.1 g (42percent yield) of the title compound.1H-NMR (DMSO-d6) δ ppm: 6.6 (s, 2H, NH2); 6.58 (s, 1H, thiazole CH); 2.9 (m, 1H, CHMe2); 1.18 (s, 3H, MeCHMe); 1.17 (s, 3H, MeCHMe).
36%	Stage #1: With bromine In 1,4-dioxane; diethyl ether at -5℃; for 2 h; Stage #2: for 16 h; Reflux	To a stirred mixture of 3-methylbutanal (2.5 g, 29 mmol) in diethyl ether/dioxane (25 ml, 0.10 ml) at -5°C was added bromine (1.64 mL, 32 mmol) over 2 h. After sustaining the bromine colour (1 h), it was neutralised with sat NaHC0₃(aq) (15 ml). The organic layer was then separated and washed with water (2 x 20 ml), brine (2 x 20 ml), dried with Na₂S0₄, filtered and concentrated in vacuo to obtain a crude residue. This residue was then added directly to a stirred solution of thiourea (2.21 g, 29 mmol) in THF (30 ml) and refluxed for 16 h. The reaction was then cooled to 20°C and quenched with sat NaHC0₃(aq) (15 ml). The THF was evaporated in vacuo and then residue dissolved in 35 ml of ethyl acetate and washed with water (2 x 20 ml), brine (2 x 20 ml), dried with Na₂S0₄, filtered and concentrated in vacuo to obtain a crude residue. The crude residue was then purified by column chromatography (100percent CyHex to 60percent EtOAc/CyHex) to obtain WIN-321-081 -01 as an oil (1.47g, 36percent). ¹H NMR (CDCI₃): δ 6.73 (d, J 1.1 Hz, 1 H), 3.00 (td, J 6.8, 1.10 Hz, 1 H), 1.27 (d, J 6.8 Hz, 6H). MS, m/z = 143 (100) [M+H]⁺.

Reference： [1] Patent: EP1124810, 2005, B1, . Location in patent: Page/Page column 12
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2764 - 2778
[3] Patent: WO2017/219083, 2017, A1, . Location in patent: Page/Page column 56
[4] Patent: WO2010/144359, 2010, A1, . Location in patent: Page/Page column 98

2
[ 64932-36-1 ]
[ 17356-08-0 ]
[ 101080-15-3 ]

Yield	Reaction Conditions	Operation in experiment
1.202 g	With triethylamine In 1,4-dioxane; ethanol; dichloromethane at 20℃; for 20 h;	To a solution of iso-valeraldehyde (1.721 g, 20 mmol)Of dichloromethane / dioxane (V / V = 4/1)A solution of bromine (1.0 mL, 20 mmol)In dichloromethane / dioxane (V / V = 4/1, 12 mL).The reaction solution was at 10 ° CTo give 2-bromoisovaleraldehyde as an intermediate.2-bromoisovaleraldehyde intermediateIn dichloromethane / dioxane was slowly added dropwise to a solution of thiourea (1.523 g, 20 mmol)Dichloromethane / dioxane (30mL), andEthanol (6 mL) and triethylamine (2.424 g, 24 mmol) were added.After reaction at room temperature for 20 h, 100 mL of distilled water was added to the reaction solution,And adjusted to pH 12 with 12N sodium hydroxide solution. After stirring at room temperature for 1 hour, the reaction mixture was extracted with methylene chloride and water. The methylene chloride layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Silica gel after column chromatography purification 5-isopropylthiazol-2-amine (e41) 1.202g, the yield of 42.26percent.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5521 - 5525
[2] European Journal of Medicinal Chemistry, 1999, vol. 34, # 10, p. 883 - 889
[3] Patent: WO2005/95367, 2005, A1, . Location in patent: Page/Page column 28
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 12, p. 4119 - 4132
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 12, p. 4119 - 4132
[6] Patent: CN105985356, 2016, A, . Location in patent: Paragraph 0137; 0138; 0139

3
[ 7664-41-7 ]
[ 590-86-3 ]
[ 101080-15-3 ]

Yield	Reaction Conditions	Operation in experiment
42%	With bromine; thiourea In 1,4-dioxane; ethanol; dichloromethane	EXAMPLE 4 Preparation of a Compound of Formula (II): 2-amino-5-isopropyl-1,3-thiazole 3-Methylbutanaldehyde (2 ml; 18.6 mmol) was dissolved in 15 ml of dioxane. A solution 2percent v/v of bromine in dioxane (47.81 ml; 18.6 mmol) was dropped therein at 0° C. The mixture was maintained at room temperature under stirring for 2 hours, then 2.83 g (37.2 mmol) of thiourea and 10 ml of ethanol were added. After 6 hours at room temperature the solution was evaporated to dryness, the residue was dissolved in methylene chloride and the product extracted with 1M hydrochloric acid; the aqueous layer was made basic by using 30percent ammonium hydrate and extracted again with methylene chloride. The organic phase was dried over sodium sulfate and evaporated under vacuum. The residue was chromatographed on a silica gel column, eluding with cyclohexane-ethylacetate to give 1.1 g (42percent yield) of the title compound. ¹H-NMR (DMSO-d⁶) δppm: 6.6 (s, 2H, NH₂); 6.58 (s, 1H, thiazole CH); 2.9 (m, 1H, CHMe₂); 1.18 (s, 3H, MeCHMe); 1.17 (s, 3H, MeCHMe).
42%	With bromine; thiourea In 1,4-dioxane; ethanol; dichloromethane	Example 1 Preparation of 2-amino-5-isopropyl-1,3-thiazole 2 ml (18.6 mmol) of 3-methylbutyraldehyde were dissolved in 15 ml of 1,4-dioxane. 40.4 ml (18.6 mmol) of a solution 2percent v/v of bromine in 1,4-dioxane was dropped therein at 0 C. The mixture was maintained at room temperature under stirring for 2 hours, then 2.83 g (37.2 mmol) of thiourea and 5 ml of ethanol were added. After 6 hours at room temperature the solution was evaporated to dryness, the residue was dissolved in CH2Cl2 and the product extracted with 1M hydrochloric acid; the aqueous layer was made basic by using 30percent ammonium hydrate and extracted again with CH2Cl2. The organic phase was dried over sodium sulfate and evaporated under vacuum. The residue was chromatographed on a silica gel column, eluding with cyclohexane-ethyl acetate to give 1.1 g (42percent yield) of the title compound. 1H-NMR (DMSO-d6) ppm: 6.6 (s, 2H, NH2); 6.58 (s, 1H, thiazole CH); 2.9 (m, 1H, CHMe2); 1.18 (s, 3H, MeCHMe); 1.17 (s, 3H, MeCHMe).

Reference： [1] Patent: US2003/187040, 2003, A1,
[2] Patent: US2005/4120, 2005, A1,

4
[ 590-86-3 ]
[ 101080-15-3 ]

Yield	Reaction Conditions	Operation in experiment
42%	With bromine; thiourea In 1,4-dioxane; CH₂Cl₂; ethanol	Example 1 Preparation of 2-amino-5-isopropyl-1,3-thiazole 2 ml (18.6 mmol) of 3-methylbutyraldehyde were dissolved in 15 ml of 1,4dioxane. 40.4 ml (18.6 mmol) of a solution 2percent v/v of bromine in 1,4-dioxane was dropped therein at 0 C. The mixture was maintained at room temperature under stirring for 2 hours, then 2.83 g (37.2 mmol) of thiourea and 5 ml of ethanol were added. After 6 hours at room temperature the solution was evaporated to dryness, the residue was dissolved in CH2Cl2 and the product extracted with 1M hydrochloric acid; the aqueous layer was made basic by using 30percent ammonium hydrate and extracted again with CH2Cl2. The organic phase was dried over sodium sulfate and evaporated under vacuum. The residue was chromatographed on a silica gel column, eluding with cyclohexane-ethyl acetate to give 1.1 g (42percent yield) of the title compound. 1H-NMR (DMSO-d6) ppm: 6.6 (s, 2H, NH2); 6.58 (s, 1H, thiazole CH); 2.9 (m, 1H, CHMe2); 1.18 (s, 3H, MeCHMe); 1.17 (s, 3H, MeCHMe).

Reference： [1] Patent: US6784198, 2004, B1,

5
[ 1119-16-0 ]
[ 17356-08-0 ]
[ 101080-15-3 ]

Reference： [1] Patent: WO2010/144394, 2010, A1, . Location in patent: Page/Page column 58-59

6
[ 590-86-3 ]
[ 101080-15-3 ]

Reference： [1] Patent: CN105985356, 2016, A,

7
[ 123-51-3 ]
[ 101080-15-3 ]

Reference： [1] Journal of Scientific and Industrial Research, 1959, vol. 18 B, p. 411

[ 101080-15-3 ] Synthesis Path-Downstream 1~46

1
[ 123-51-3 ]
[ 101080-15-3 ]

Reference： [1]Journal Of Scientific and Industrial Research,1959,vol. 18 B,p. 411

2
[ 101080-15-3 ]
[ 98-59-9 ]
[ 94680-54-3 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 247 - 257

3
[ 10531-41-6 ]
[ 101080-15-3 ]
2-(2-imino-5-isopropyl-thiazol-3-yl)-1-thiophen-2-yl-ethanone; hydrobromide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 883 - 889

4
[ 101080-15-3 ]
[ 70-11-1 ]
2-(2-imino-5-isopropyl-thiazol-3-yl)-1-phenyl-ethanone; hydrobromide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 883 - 889

5
[ 64932-36-1 ]
[ 17356-08-0 ]
[ 101080-15-3 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; ethanol; at 20℃; for 16h;	3-Methyl-butyraldehyde (174 mmol) was dissolved in 400 mL of anhydrous dioxane and cooled to 0C under N2. In a separate flask, bromine (174 mmol) was dissolved in 500 mL of anhydrous dioxane. The bromine-dioxane solution was added drop wise to the reaction solution, maintaining the 0C temperature. A colorless precipitate formed. Once the addition was complete, the reaction was warmed to rt and stirred for 2 h. A slurry of thiourea (244 mmol) in 80 mL of anhydrous ethanol was then added to the reaction and the suspension was stirred at rt for an additional 16 h. The crude reaction was then filtered to remove solids and the filtrated was concentrated under reduced pressure to give a residual oil. This oil was partitioned between 200 mL of EtOAc and 200 mL of 1N NaOH aqueous solution and extracted. The organics were further washed with 200 mL of water, and 200 mL of brine. The organics were then dried over Na2SO4, filtered and concentrated under reduced pressure to give 5-lsopropyl-thiazol-2-ylamine as the desired product. The crude material was purified through flash chromatography on silica gel and used directly
1.202 g	With triethylamine; In 1,4-dioxane; ethanol; dichloromethane; at 20℃; for 20h;	To a solution of iso-valeraldehyde (1.721 g, 20 mmol)Of dichloromethane / dioxane (V / V = 4/1)A solution of bromine (1.0 mL, 20 mmol)In dichloromethane / dioxane (V / V = 4/1, 12 mL).The reaction solution was at 10 CTo give 2-bromoisovaleraldehyde as an intermediate.2-bromoisovaleraldehyde intermediateIn dichloromethane / dioxane was slowly added dropwise to a solution of thiourea (1.523 g, 20 mmol)Dichloromethane / dioxane (30mL), andEthanol (6 mL) and triethylamine (2.424 g, 24 mmol) were added.After reaction at room temperature for 20 h, 100 mL of distilled water was added to the reaction solution,And adjusted to pH 12 with 12N sodium hydroxide solution. After stirring at room temperature for 1 hour, the reaction mixture was extracted with methylene chloride and water. The methylene chloride layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Silica gel after column chromatography purification 5-isopropylthiazol-2-amine (e41) 1.202g, the yield of 42.26%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5521 - 5525
[2]European Journal of Medicinal Chemistry,1999,vol. 34,p. 883 - 889
[3]Patent: WO2005/95367,2005,A1 .Location in patent: Page/Page column 28
[4]Journal of Medicinal Chemistry,2011,vol. 54,p. 4119 - 4132
[5]Journal of Medicinal Chemistry,2011,vol. 54,p. 4119 - 4132
[6]Patent: CN105985356,2016,A .Location in patent: Paragraph 0137; 0138; 0139

7
[ 101080-15-3 ]
[ 122-51-0 ]
[ 762-04-9 ]
[(diethoxy-phosphoryl)-(5-isopropyl-thiazol-2-ylamino)-methyl]-phosphonic acid diethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3721 - 3738

8
[ 103-82-2 ]
[ 101080-15-3 ]
BML-259 [ No CAS ]