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[ CAS No. 855531-21-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 855531-21-4
Chemical Structure| 855531-21-4
Chemical Structure| 855531-21-4
Structure of 855531-21-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 855531-21-4 ]

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Product Details of [ 855531-21-4 ]

CAS No. :855531-21-4 MDL No. :MFCD08166421
Formula : C10H7ClN2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :MJKAKAOPNKDQNN-UHFFFAOYSA-N
M.W :254.69 Pubchem ID :34177982
Synonyms :

Calculated chemistry of [ 855531-21-4 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 63.63
TPSA : 90.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 3.32
Log Po/w (WLOGP) : 3.24
Log Po/w (MLOGP) : 1.72
Log Po/w (SILICOS-IT) : 2.87
Consensus Log Po/w : 2.57

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.82
Solubility : 0.0384 mg/ml ; 0.000151 mol/l
Class : Soluble
Log S (Ali) : -4.9
Solubility : 0.00324 mg/ml ; 0.0000127 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.86
Solubility : 0.0354 mg/ml ; 0.000139 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.5

Safety of [ 855531-21-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 855531-21-4 ]

* 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 [ 855531-21-4 ]

[ 855531-21-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 855531-21-4 ]
  • [ 89-75-8 ]
  • [ 855531-33-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 20℃; for 2h; 136 A mixture of 2.0 g (7.8 mmol) 2- (4-Chloro-phenylamino)-thiazole-5-carboxylic acid, 1.65 ml (11.8 mmol) 2,4-Dichlorobenzoyl chloride and 3.27 ml (23.5 mmol) NEt3 in 30 ml DCM was stirred at toom temperature for 2 h and evaporated to dryness. The intermediately built 2- [ (2, 4-Dichloro-benzoyl)- (4-chloro-phenyl)-amino]-thiazole-5- carboxylic acid was identified by MS analysis (m/e): 429.0 (M+H+, 100%) and used without further purification in the consecutive step. A mixture of 30 mg (0.07 mmol) 2- [ (2, 4-Dichloro-benzoyl)- (4-chloro-phenyl)-amino]-thiazole-5-carboxylic acid, 14.8 mg (0.091 mmol) Carbonyldimimidazole and 12.5 mg (0.175 mmol) pyrrolidine in 1.2 ml DMF was stirred at room temperature for 16 h. The mixture was directly subjected to reversed phase HPLC purification eluting with an acetonitrile/water gradient to yield after evaporation of the product fractions 17.9 mg (53 %) of the title compound. MS (m/e): 482.0 (MH+, 100%) According to the procedure described fort he synthesis of Example 136 further derivatives have been synthesised from 2- [ (4-Chloro-phenyl)- (2, 4-dichloro-benzoyl) - amino]-thiazole-5-carboxylic acid and various commercially available amines and comprise Examples 137-Example 146 below. In cases of Example 143 additionally 2 eq. NEt3 were added to the reaction mixture as the amine hydochloride was used as starting material.
  • 2
  • [ 855531-18-9 ]
  • [ 855531-21-4 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 2-(4-chloro-phenylamino)-thiazole-5-carboxylic acid ethyl ester With potassium hydroxide In tetrahydrofuran; methanol at 50℃; for 4h; Stage #2: With acetic acid In water 1.R A mixture of 3.0 g (11. 1 mmol) 2- (4-Chloro-phenylamino)-thiazole-5-carboxylic acid ethyl ester and 6.7 ml 5M KOH in 50 ml THF and 10 ml MeOH was heated to 50 °C for 4 h and subsequently concentrated. The residue was taken up in water, acidified with acetic acid and extracted with ethyl acetat. The combined organic layers were washed with water, dried with MgS04 and evaporated. The residue was recrystallised from ethyl acetate to obrain 2.0 g (70 %) of the title compound as white crystals. (m/e): 254.9 (M+H+, 100%)
  • 3
  • [ 855531-21-4 ]
  • [ 55899-42-8 ]
  • [ 1072930-70-1 ]
YieldReaction ConditionsOperation in experiment
4% Stage #1: 2-(4-chloro-phenylamino)-thiazole-5-carboxylic acid; N-propylbenzene-1,2-diamine With PPA (polyphosphoric acid) at 210℃; for 0.333333h; Microwave irradiation; Stage #2: With sodium hydroxide In water 112 (4-Chloro-phenyl)-[5-(1-propyl-1H-benzoimidazol-2-yl)-thiazol-2-yl]-amine EXAMPLE 112 (4-Chloro-phenyl)-[5-(1-propyl-1H-benzoimidazol-2-yl)-thiazol-2-yl]-amine A mixture of 2-(4-Chlorophenylamino)-5-thiazolecarboxylic acid (300 mg, 1.18 mmol) and N-propyl-benzene-1,2-diamine (212 mg, 1.41 mmol) in PPA (5 ml) was heated to 210° C. in a microwave oven for 20 min. The mixture was then poured onto water and the pH of the solution was adjusted to 10 with an aq. soln. of 2N NaOH, and the mixture was extracted with DCM. The combined org. layers were dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (DCM/MeOH 100:0 to 94:6) afforded the desired product (16 mg, 4%). HPLC (System 2, 10-100% CH3CN): tR=3.270 min, MS (LC-MS): 369 [M+1].
4% With PPA; Polyphosphoric acid (PPA) at 210℃; for 0.333333h; Microwave irradiation; 112 Example 112: (4-Chloro-phenyl)-[5-(1 -propyl-1 H-benzoimidazol-2-yl)-thiazol-2-yl]-amine A mixture of 2-(4-Chlorophenylamino)-5-thiazolecarboxylic acid (300 mg, 1.18 mmol) and N-propyl-benzene-1 ,2-diamine (212 mg, 1.41 mmol) in PPA (5 ml) was heated to 210 0C in a microwave oven for 20 min. The mixture was then poured onto water and the pH of the solution was adjusted to 10 with an aq. soln. of 2N NaOH, and the mixture was extracted with DCM. The combined org. layers were dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (DCIWMeOH 100:0 to 94:6) afforded the desired product (16 mg, 4%). HPLC (System 2, 10-100% CH3CN): tR = 3.270 min, MS (LC-MS): 369 [M+1].
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