[ CAS No. 221681-75-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 221681-75-0 * Storage: {[proInfo.prStorage]}

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Login	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}	Login		Inquiry

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 221681-75-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 221681-75-0 ]

SDS Specification

Alternatived Products of [ 221681-75-0 ]

Product Details of [ 221681-75-0 ]

CAS No. :	221681-75-0	MDL No. :	MFCD08690108
Formula :	C₇H₆ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZUCDYBREEPULBI-UHFFFAOYSA-N
M.W :	167.60	Pubchem ID :	22022411
Synonyms :

Calculated chemistry of [ 221681-75-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.51
TPSA :	54.7 ?2

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) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.91
Log Po/w (XLOGP3) :	1.5
Log Po/w (WLOGP) :	1.81
Log Po/w (MLOGP) :	1.11
Log Po/w (SILICOS-IT) :	1.95
Consensus Log Po/w :	1.46

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.43
Solubility :	0.623 mg/ml ; 0.00372 mol/l
Class :	Soluble
Log S (Ali) :	-2.26
Solubility :	0.929 mg/ml ; 0.00554 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.16
Solubility :	0.116 mg/ml ; 0.00069 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.47

Safety of [ 221681-75-0 ]

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 [ 221681-75-0 ]

* 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 [ 221681-75-0 ]

[ 221681-75-0 ] Synthesis Path-Downstream 1~17

1
[ 101420-98-8 ]
[ 221681-75-0 ]

Reference： [1]Journal of the Chemical Society,1955,p. 2412,2419

2
[ 267891-86-1 ]
[ 221681-75-0 ]
[ 381694-55-9 ]

Reference： [1]Patent: EP1280799,2004,B1 .Location in patent: Page/Page column 8

3
[ 864082-31-5 ]
[ 221681-75-0 ]
N-(6-chloro-1H-indazol-5-yl)-4-(4-chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 20.0℃; for 18.0h;	Example 55;. N- (6-Chloro-lH-indazol-5-yl)-4- (4-chlorophenyl)-2-methyl-6-oxo- 1, 4,5, 6-tetrahydro-3-pyridinecarboxamide;. 6-Chloro-lH-indazol-5-amine (64 mg, 0.382 mmol, 1.0 equiv) was combined with the product from Example 4, Step 2 (101 mg, 0. 382 mmol, 1.0 equiv), EDC (88 mg, 0.458 mmol, 1.2 equiv) and Et3N (64, ut, 0.458 mmol, 1.2 equiv) in DMF (ImL) and stirred at room temperature for 18 hours. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HC1, once with satd. NaHC03, and once with satd. NaCl. The organic phase was concentrated en vacuo. The residue was purified by flash chromatography (0-100% EtOAc in Hexanes) and further purified by reverse-phase HPLC (15-98% CH3CN/H20, adjusted to pH 10 w/NH40H over 13 minutes, retention time 6.56 min) to provide 40 mg (25%) of the title compound as a white solid. MS (ES+) m/e 416 [M+H]+

Reference： [1]Patent: WO2005/82890,2005,A1 .Location in patent: Page/Page column 64

4
[ 267891-86-1 ]
O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium [ No CAS ]
[ 221681-75-0 ]
[ 381694-55-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; In N-methyl-acetamide; water;	EXAMPLE 2 N-(6-Chloroindazol-5-yl)-2-[(4-pyridyl)methyl]amino-Benzoic Acid Amide 194 mg (0.85 mmol) of 2-(4-pyridylmethyl)aminobenzoic acid is mixed in 8 ml of dimethylformamide with 283 mg (1.69 mmol) of <strong>[221681-75-0]5-amino-6-chloroindazole</strong>. Under argon and in a moisture-free environment, 215 mg (2.13 mmol) of N-methylmorpholine and 386 mg (1.02 mmol) of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophophate are added to this solution. This mixture is stirred for 4 hours at room temperature. It is then diluted with about 40 ml of water and extracted three times with 30 ml of ethyl acetate each. The combined organic phase is washed with water, dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride:ethanol-10:1 as an eluant. 97 mg (30.2% of theory) of N-(6-chloroindazol-5-yl)-2-[(4-pyridyl)methyl]amino-benzoic acid amide with a melting point of 222.8 C. is obtained. Similarly produced are:

Reference： [1]Patent: US2004/102441,2004,A1

5
(RS)-ethyl 4-chloro-5, 6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylate [ No CAS ]
[ 221681-75-0 ]
ethyl 4-[(6-chloro-1H-indazol-5-yl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35 mg	With hydrogenchloride; In 1,4-dioxane; ethanol; for 16.0h;Molecular sieve; Reflux;	To a mixture of ethyl 4-(1 H-indazol-5-ylamino)-5, 6,7,8- tetrahydro[1 ]benzothieno[2, 3-d]pyrimidine-7-carboxylate (650 mg) and 5-amino-6- chloroindazole (422 mg, 1 .15 eq) in ethanol (8.0 mL) were added 4A molecular sieves (2 g), followed by a 4 N solution of hydrogen chloride in dioxane (821 muIota_, 1 .5 eq). The mixture was heated to reflux for 16 h and added to water after cooling to room temperature. The precipitate was isolated by filtration and triturated with DMSO. Insolubles were removed by filtration, the filtrate was concentrated in vacuo to give the crude product which was purified by preparative HPLC (Method P4) yielding 35 mg of the target compound.1H-NMR (300MHz, DMSO-d6): delta [ppm]= 1 .22 (t, 3H), 1 .89 - 2.05 (m, 1 H), 2.16 - 2.31 (m, 1 H), 2.89 - 3.30 (m, 5H, partly overlapped with water signal), 4.14 (q, 2H), 7.77 (s, 1 H), 8.07 - 8.16 (m, 2H), 8.25 (s, 1 H), 8.29 (s, 1 H), 13.21 (br. s. , 1 H).MS (ESIpos) m/z = 428 (35Cl), 430 (37Cl) [M+H]+.

Reference： [1]Patent: WO2013/174744,2013,A1 .Location in patent: Page/Page column 99; 100

6
[ 24424-99-5 ]
[ 221681-75-0 ]
tert-butyl 5-amino-6-chloro-1H-indazole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 25.0℃; for 18.0h;	Intermediate 12-1 tert-Butyl 5-amino-6-chloro-1H-indazole-1-carboxylate (1275) (1276) 2.1 ml (11.8 mmol) of N,N-diisopropylethylamine and 2.34 g (10.7 mmol) of di-tert-butyl dicarbonate were added to 1.80 g (10.7 mmol) of <strong>[221681-75-0]6-chloro-1H-indazole-5-amine</strong> (CAS No. 221681-75-0) in 18 ml of tetrahydrofuran, and the mixture was stirred at 25 C. for 18 h. The mixture was concentrated and the residue was taken up in ethyl acetate and, during concentration, adsorbed on Isolute. The Isolute was applied to a Biotage SNAP cartridge (100 g; KP-Sil) pre-equilibrated with hexane and chromatography was carried out using the Isolera flash purification system (Biotage) (mobile phase: hexane/ethyl acetate; flow rate: 50 ml/min; gradient: isocratic 100:0 (5 min), 100:0->75:25 (20 min), isocratic 75:25 (5 min), 75:25->50:50 (15 min), isocratic 50:50 (5 min), 50:50->0:100 (15 min)) The combined product fractions were concentrated and dried under reduced pressure. This gave 1.23 g (43% of theory) of the title compound. (1277) UPLC-MS (Method A1): Rt=1.16 min (1278) MS (ESIpos): m/z=268 (M+H)+

Reference： [1]Patent: US2016/311833,2016,A1 .Location in patent: Paragraph 1275; 1276; 1277; 1278

7
[ 221681-75-0 ]
N-(6-chloro-2-{2-oxo-2-[(3R)-piperidin-3-ylamino]ethyl}-2H-indazol-5-yl)-6-(trifluoromethyl)pyridine-2-carboxamide [ No CAS ]