[ CAS No. 27328-69-4 ]

Name: 27328-69-4|5-Chloro-3-(chloromethyl)-1H-indazole|97%
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3d Animation Molecule Structure of 27328-69-4

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Quality Control of [ 27328-69-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 27328-69-4 ]

CAS No. :	27328-69-4	MDL No. :	MFCD24458996
Formula :	C₈H₆Cl₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	201.05 g/mol	Pubchem ID :	14062703
Synonyms :

Calculated chemistry of of [ 27328-69-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.87
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.45
Log Po/w (XLOGP3) :	2.61
Log Po/w (WLOGP) :	2.8
Log Po/w (MLOGP) :	2.34
Log Po/w (SILICOS-IT) :	3.6
Consensus Log Po/w :	2.56

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.22
Solubility :	0.121 mg/ml ; 0.000603 mol/l
Class :	Soluble
Log S (Ali) :	-2.86
Solubility :	0.276 mg/ml ; 0.00137 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.55
Solubility :	0.00563 mg/ml ; 0.000028 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 27328-69-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	1759
Hazard Statements:	H302-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 27328-69-4 ]

* 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 [ 27328-69-4 ]

[ 27328-69-4 ] Synthesis Path-Downstream 1~31

1
[ 64605-36-3 ]
[ 27328-69-4 ]

Yield	Reaction Conditions	Operation in experiment
56%		To a stirred suspension of 2-amino-5-chloro-?-chloroacetophenone (670 mg, 3,28 mmol) in conc. hydrochloric acid (10 mL) is added a solution of sodium nitrite (250 mg, 3,61 mmol) in water (2 mL) while maintaining the reaction temperature at 0 C. After 1 h a solution of SnCl2.2H2O (1,78 g, 7,87 mmol) in conc. hydrochloric acid (5 mL) is added to the reaction mixture, which is then stirred at the same temperature for 1 h. Next, ice water is added to the reaction mixture. The precipitate is collected by filtration, washed with water and dried giving crude 5-chloro-3-(chloromethyl)-1H-indazole (370 mg, 1,84 mmol, 56% yield) which is used in the next step without further purification. LC/MS (I) (5-95%, 5 min): 2.67, no mass peak.
		The title compound was prepared in a similar manner as described in J. Org. Chem, 1979, 44, 578: To a suspension of 1 -(2-amino-5-chlorophenyl)-2-chloroethanone (1 .35 g, 6.63 mmol) in HCI 37% in water was added dropwise at -10C a solution of Sodium nitrite (0.503 g, 7.29 mmol) in H20 (3.1 ml). The reaction mixture was stirred at this temperature during 1 h, then a solution of Tin (II) chloride (3.02 g, 15.91 mmol) in HCI 37% in H20 (9.2 ml) was added and the reaction mixture was stirred 1 h at the same temperature. Ice-water was added and the precipitate formed was filtered, washed with ice-water and dried on HV. UPLC RtE= 0.89 min, [M+H]+ = 201 .1 -203.1 .
		To a stirred suspension of l-(2-amino-5-chlorophenyl)-2-chloroethanone (16 g, 78 mmol, 1.0 eq) in cone, hydrochloric acid (120 mL) was added a solution of sodium nitrite (5.9 g, 86 mmol, 1.1 eq) in water (30 mL) at 0 C. After 1 h, a solution of SnCl22H20 (42.3 g, 187 mmol, 2.4 eq) in cone, hydrochloric acid (60 mL) was added to the reaction mixture and stirred for 1 h. Ice-water was added to the reaction mixture. The precipitate was collected by filtration, washed with water and dried to afford crude 5-chloro-3-(chloromethyl)- lH-indazole, which was used in the next step without further purification (13.5 g, 86%).

Step 2; 0 ci CI NaN02, SnCl2 C zon /y conc. HCI I/' nu2 N 5-chloro-3- (chloromethv)-1 H-indazole To a stirred suspension of 2-amino-5-chloro-a-chloroacetophenone (670 mg, 3.28 mmol) in conc. hydrochloric acid (10 mL) is added a solution of sodium nitrite (250 mg, 3.61 mmol) in water (2 mL) while mantaining the reaction temperature at 0 C. After 1 h a solution of SnCI2a2H2O (1.78 g, 7.87 mmol) in conc. hydrochloric acid (5 mL) is added to the reaction mixture, which is then stirred at the same temperature for 1 h. Next, ice water is added to the reaction mixture. The precipitate is collected by filtration, washed with water and dried giving crude 5-chloro-3-(chloromethyl)-1H-indazole which is used in the next step without further purification. LC/MS (la) 2.67, no mass peak.

Reference： [1]Patent: EP1674464,2006,A1 .Location in patent: Page/Page column 14; 16-17
[2]Synthetic Communications,1988,vol. 18,p. 259 - 264
[3]Patent: WO2013/111108,2013,A1 .Location in patent: Page/Page column 43
[4]Patent: WO2015/103317,2015,A1 .Location in patent: Page/Page column 42
[5]Patent: WO2005/95343,2005,A1 .Location in patent: Page/Page column 50-51

2
[ 27328-69-4 ]
[ 118511-95-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium azide; In water; N,N-dimethyl-formamide; at 90℃; for 1h;	A stirred solution containing <strong>[27328-69-4]5-chloro-3-(chloromethyl)-1H-indazole</strong> (370 mg, 1,84 mmol), sodium azide (156 mg, 2,40 mmol), water (0,5 mL) and DMF (5,00 mL) is warmed at 90 C for 1 h and then the mixture is concentrated under reduced pressure. Ice is added and the resulting precipitate is collected by filtration and washed with water giving 330 mg (1,59 mmol, 85% yield) of 3-(azidomethyl)-5-chloro-1H-indazole. LC/MS (I) (5-95%, 5 min): 2.63, 249 (M+H+AcCN).
	With sodium azide; In water; N,N-dimethyl-formamide; at 90℃; for 1h;	The title compound was prepared in a similar manner as described in Synthetic Communications, 1988, 18(3), 259-264: To a solution of 5-chloro-3-(chloromethyl)-1 H- indazole (1 .26 g, 6.28 mmol) in DMF (12.6 ml) and H20 (1.3 ml) was added Sodium azide (0.53 g, 8.16 mmol). The reaction mixture was stirred at 90C during 1 h. Volatiles were evaporated and the crude residue was diluted with ice-water (50 ml) and brine (50 ml), extracted with EtOAc (4 x 50 ml). The combined organic layers were dried (Na2S04), filtered and concentrated. The crude residue was engaged in the next step without further purification. UPLC RtE= 0.90 min, [M+H]+ = 206.2-208.3.
	With sodium azide; In water; N,N-dimethyl-formamide; at 90℃; for 1h;	Step 3; 3-(Azidomethyl)-5-chloro-1 H-indazole. A stirred solution containing <strong>[27328-69-4]5-chloro-3-(chloromethyl)-1H-indazole</strong> (370 mg, 1.84 mmol), sodium azide (156 mg, 2.40 mmol), water (0.5 mL) and N, N-dimethylformamide (5.00 mL) is warmed at 90 C for 1 h and then the mixture is concentrated under reduced pressure. Ice is added and the resulting precipitate is collected by filtration and washed with water giving the 3- (azidomethyl)-5-chloro-1 H-indazole. LC/MS (la) rt 2. 63,249 (M+H+AcCN) +.

Reference： [1]Synthetic Communications,1988,vol. 18,p. 259 - 264
[2]Patent: EP1674464,2006,A1 .Location in patent: Page/Page column 14; 17
[3]Patent: WO2013/111108,2013,A1 .Location in patent: Page/Page column 43-44
[4]Patent: WO2005/95343,2005,A1 .Location in patent: Page/Page column 51

4
[ 106-47-8 ]
N,N-diethyl-N-<2-chloro-quinazolin-4-yl>-N'-methyl-ethylenediamine [ No CAS ]
[ 27328-69-4 ]

Reference： [1]Synthetic Communications,1988,vol. 18,p. 259 - 264

5
[ 27328-69-4 ]
[ 118511-97-0 ]

Reference： [1]Synthetic Communications,1988,vol. 18,p. 259 - 264
[2]Patent: WO2013/111108,2013,A1
[3]Patent: WO2005/95343,2005,A1

6
[ 106-47-8 ]
[ 27328-69-4 ]

Reference： [1]Patent: WO2013/111108,2013,A1
[2]Patent: WO2015/103317,2015,A1
[3]Patent: WO2005/95343,2005,A1

7
[ 27328-69-4 ]
[ 1448725-50-5 ]

Reference： [1]Patent: WO2013/111108,2013,A1

8
[ 110-87-2 ]
[ 27328-69-4 ]
5-chloro-3-(chloromethyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16 g	With toluene-4-sulfonic acid; In tetrahydrofuran; at 70℃; for 12h;	A solution of 5-chloro-3-(chloromethyl)-lH-indazole (13.5 g, 67 mmol, 1.0 eq), 3,4-dihydro-2H-pyran (11.3 g, 134 mmol, 2.0 eq) and p-toluenesulfonic acid monohydrate (1.27 g, 6.7 mmol, 0.1 eq) in THF (300 mL) was stirred at 70 C for 12 h. After cooling to rt (~22 C), the reaction mixture was mixed with water (300 mL) and extracted with EA (200 mL x2). The organic layer was washed with brine, dried over anhydrous Na2S04, and concentrated to afford 5-chloro-3-(chloromethyl)-l -(tetrahydro-2H-pyran-2-yl)-lH-indazole as a yellow solid (16 g, 84%

Reference： [1]Patent: WO2015/103317,2015,A1 .Location in patent: Page/Page column 42

9
[ 27328-69-4 ]
N-((5-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)methyl)-1-(4-((2-oxopyridin-1(2H)-yl)methyl)benzyl)-1H-indole-3-carboxamide [ No CAS ]