[ CAS No. 89281-44-7 ] {[proInfo.proName]}

Name: 89281-44-7|2-Methylthiazol-5-amine|95%
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Quality Control of [ 89281-44-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 89281-44-7 ]

CAS No. :	89281-44-7	MDL No. :	MFCD11847087
Formula :	C₄H₆N₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IDSUZAVUCMIBBS-UHFFFAOYSA-N
M.W :	114.17	Pubchem ID :	20829880
Synonyms :

Calculated chemistry of [ 89281-44-7 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.48
TPSA :	67.15 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) :	-6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.28
Log Po/w (XLOGP3) :	1.01
Log Po/w (WLOGP) :	1.04
Log Po/w (MLOGP) :	-0.61
Log Po/w (SILICOS-IT) :	1.91
Consensus Log Po/w :	0.93

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.71
Solubility :	2.21 mg/ml ; 0.0194 mol/l
Class :	Very soluble
Log S (Ali) :	-2.01
Solubility :	1.12 mg/ml ; 0.00979 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.26
Solubility :	6.2 mg/ml ; 0.0543 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.15

Safety of [ 89281-44-7 ]

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

Application In Synthesis of [ 89281-44-7 ]

* 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.

Downstream synthetic route of [ 89281-44-7 ]

[ 89281-44-7 ] Synthesis Path-Downstream 1~20

1
[ 89281-44-7 ]
[ 108-24-7 ]
[ 6449-69-0 ]

Reference： [1]Journal of general chemistry of the USSR,1964,vol. 34,p. 2080 - 2085
Zhurnal Obshchei Khimii,1964,vol. 34,p. 2068 - 2074

2
[ 594-03-6 ]
[ 540-61-4 ]
[ 89281-44-7 ]

Reference： [1]Journal of general chemistry of the USSR,1964,vol. 34,p. 2080 - 2085
Zhurnal Obshchei Khimii,1964,vol. 34,p. 2068 - 2074

4
5-amino-2-methyl-thiazole-carboxylic acid-⁽⁴⁾-amide [ No CAS ]
[ 89281-44-7 ]

Reference： [1]Monatshefte fur Chemie,1895,vol. 16,p. 742

5
[ 870-73-5 ]
[ 151-63-3 ]
[ 89281-44-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; at 15 - 25℃; for 32h;pH 9;Heating / reflux;	Ethyl dithioacetate (5.24 g, 0.044 mol) and aminoacetonitrile hydrogensulfate (7.4 g, 0.048 mol) are dissolved in EtOH. The pH is adjusted to pH 9 with NaOH. The reaction is stirred at RT for 24 h, then heated under reflux. After 8 h, the reaction is cooled, diluted with aqueous NaOH and extracted with EtOAc. The combined organic layers are dried (MgSO4), filtered and concentrated. The residue is purified by chromatography (Biotage 40M, EtOAc) to provide 1.04 g of 5-amino-2-methylthiazole. MS (ESI) for C4H6N2S (M+H)+ m/z 115. Example 141 is obtained from 5-chloro-2,4-dimethoxyphenyl isocyanate and 5-amino-2-methylthiazole according to Method A, making non-critical variations. Yield 17%. HRMS (FAB) calcd for C13H14ClN3O3S+H 328.0522, found 328.0528.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4794 - 4797
[2]Patent: US2003/236287,2003,A1 .Location in patent: Page 33

6
[ 89281-44-7 ]
[ 55440-55-6 ]
N-(5-chloro-2,4-dimethoxyphenyl)-N'-(2-methyl-1,3-thiazol-5-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%		Ethyl dithioacetate (5.24 g, 0.044 mol) and aminoacetonitrile hydrogensulfate (7.4 g, 0.048 mol) are dissolved in EtOH. The pH is adjusted to pH 9 with NaOH. The reaction is stirred at RT for 24 h, then heated under reflux. After 8 h, the reaction is cooled, diluted with aqueous NaOH and extracted with EtOAc. The combined organic layers are dried (MgSO4), filtered and concentrated. The residue is purified by chromatography (Biotage 40M, EtOAc) to provide 1.04 g of <strong>[89281-44-7]5-amino-2-methylthiazole</strong>. MS (ESI) for C4H6N2S (M+H)+ m/z 115. Example 141 is obtained from 5-chloro-2,4-dimethoxyphenyl isocyanate and <strong>[89281-44-7]5-amino-2-methylthiazole</strong> according to Method A, making non-critical variations. Yield 17%. HRMS (FAB) calcd for C13H14ClN3O3S+H 328.0522, found 328.0528.

Reference： [1]Patent: US2003/236287,2003,A1 .Location in patent: Page 33

7
[ 870-73-5 ]
[ 89281-44-7 ]

Yield	Reaction Conditions	Operation in experiment
52%		Method 2; 2-Methgammal- 1 ,3-thiazol-5-amine; To a solution of aminoacetonitrile bisulfate (6.4 g, 41.6 mmol) in anhydrous MeOH (75 ml) at O0C was added Et3N (11.6 mL, 83mmol). After 30 minutes, ethyl dithioacetate (5g, 41.6 mmol) was added and the resulting dark orange solution stirred at room temperature for 2 hours. Half the solvent was removed under reduced pressure. The solution was diluted with an equivalent volume of EtOAc, washed with water, and dried (Na2SO4). The solvents were removed under reduced pressure and the residue slurried in warm EtOAc, cooled in an ice bath, and filtered to give 2.45g (52%) of a brown solid. 1H NMR DMSO-d6: 6.62 (s, 1 H) 5.36 (bs, 2 H) 2.89 (s, 3 H); m/z: 115.

Reference： [1]Patent: WO2007/71955,2007,A1 .Location in patent: Page/Page column 48

8
[ 89281-44-7 ]
[ 896160-38-6 ]
5-[3-(1-cyano-1-methylethyl)benzoyl]amino}-2-methyl-N-(2-methyl-1,3-thiazol-5-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 16h;	Example 1; 5- { [3 -( 1 -Cyano- 1 -methylethyDbenzoyl] amino > -2-methyl-N-f 2-methyl- 1 ,3 -thiazol-5- vDbenzamide; A solution of 5-[3-(l-cyano-l-methylethyl)benzoyl]amino}-2-methylbenzoic acid (Method 7, 82 mg, 0.25 mmol), 2-methyl-l,3-thiazol-5-amine (Method 2, 28 mg, 0.25 mmol), HATU (101 mg, 0.275 mmol) and lambdazetaN-diisopropylethylamine (0.135 mL) in DMF (0.5 mL) was stirred for 16 hours at room temperature. The reaction mixture was partitioned between water and EtOAc, and the organic layer was washed with brine and dried (MgSO4). <n="59"/>Purification by reverse HPLC (5%-95% water-MeCN, 15 minutes) afforded 51mg (48%) of title compound after evaporation of the solvents.1H NMR CDCl3 11.80 (s, 1 H) 10.39 (s, 1 H) 8.64 (s, 1 H) 7.90 - 8.02 (m, 3 H) 7.78- 7.81 (m, 2 H) 7.60 (t, 1 H) 7.35 (d, 1 H) 2.49 (s, 3H) 2.39 (s, 3 H) 1.76 (s, 6 H); m/z 419.

Reference： [1]Patent: WO2007/71955,2007,A1 .Location in patent: Page/Page column 57-58

9
[ 89281-44-7 ]
[ 143617-90-7 ]
tert-butyl (4-methyl-3-[(2-methyl-1,3-thiazol-5-yl)amino]carbonyl}phenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridine; HATU; In N,N-dimethyl-formamide; for 16h;	Example 84; fert-Butyl (4-methyl-3-{r(2-methyl-l,3-thiazol-5-yl)aminolcarbonyUphenyl)carbamate; To a solution of 5-[(tert-butoxycarbonyl)amino]-2-methylbenzoic acid (Method 27, 2.9 g, 11.5 mmol) and 2-methyl-l,3-thiazol-5-amine (Method 2, 1.3 g, 11.4 mmol) in anhydrous DMF (10 ml) was added HATU (4.4 g, 11.6 mmol) and pyridine (4.6 ml, 56.9 mmol, 5 eq.). After stirring for 16 hours, the reaction mixture was diluted with EtOAc, washed with water, dried (Na2SO4) and concentrated. Purification by chromatography gave 3.4 g (85%) of a white solid. 1H NMR 11.54 (s, 1 H), 9.46 (s, 1 H), 7.62 (s, 1 H), 7.39 - 7.42 (m, 2 H), 7.18 (d, 1 H), 2.56 (s, 3 H), 2.29 (s, 3 H) 1.47 (s, 9 H); m/z: 348.

Reference： [1]Patent: WO2007/71955,2007,A1 .Location in patent: Page/Page column 75
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4794 - 4797

10
[ 89281-44-7 ]
[ 896160-35-3 ]
2-chloro-N-(2-methyl-1,3-thiazol-5-yl)-5-[3-(trifluoromethyl)benzoyl]amino}benzamide [ No CAS ]