[ CAS No. 59673-74-4 ] {[proInfo.proName]}

Name: 59673-74-4|6-Amino-1H-indazol-3-ol|95%
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SKU: A103630
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Quality Control of [ 59673-74-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 59673-74-4 ]

SDS Specification

Alternatived Products of [ 59673-74-4 ]

Product Details of [ 59673-74-4 ]

CAS No. :	59673-74-4	MDL No. :	MFCD07781650
Formula :	C₇H₇N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RVEOZWSYDIHKIB-UHFFFAOYSA-N
M.W :	149.15	Pubchem ID :	108801
Synonyms :

Calculated chemistry of [ 59673-74-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	3.0
Molar Refractivity :	42.52
TPSA :	74.93 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.35
Log Po/w (XLOGP3) :	0.85
Log Po/w (WLOGP) :	0.86
Log Po/w (MLOGP) :	0.6
Log Po/w (SILICOS-IT) :	0.83
Consensus Log Po/w :	0.7

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.91
Solubility :	1.85 mg/ml ; 0.0124 mol/l
Class :	Very soluble
Log S (Ali) :	-2.01
Solubility :	1.47 mg/ml ; 0.00985 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.96
Solubility :	1.65 mg/ml ; 0.011 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.79

Safety of [ 59673-74-4 ]

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 [ 59673-74-4 ]

* 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.

Upstream synthesis route of [ 59673-74-4 ]
Downstream synthetic route of [ 59673-74-4 ]

[ 59673-74-4 ] Synthesis Path-Upstream 1~1

1
[ 7364-33-2 ]
[ 59673-74-4 ]

Reference： [1] Journal of the Chemical Society, 1955, p. 2412,2419
[2] Chemische Berichte, 1942, vol. 75, p. 1096,1104

[ 59673-74-4 ] Synthesis Path-Downstream 1~24

1
[ 7364-33-2 ]
[ 59673-74-4 ]

Reference： [1]Journal of the Chemical Society,1955,p. 2412,2419
[2]Chemische Berichte,1942,vol. 75,p. 1096,1104

2
[ 59673-74-4 ]
4-bromo-Ν-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine [ No CAS ]
4-bromo-Ν-α-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-Ν-(3-oxo-2,3-dihydro-1H-indazol-6-yl)-L-phenylalaninamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide; at 20.0℃; for 16.0h;	A solution of 4-bromo-Nu-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine (1500 mg, 3 mmol) and <strong>[59673-74-4]6-amino-1,2-dihydro-3H-indazol-3-one</strong> (555 mg, 24 mmol) in ethyl acetate (21 ml) was treated with N, N-diisopropylethylamine (1.4 ml, 7.8 mmol).The suspension was treated with a 2,4, 6-tripropyl-l, 3,5,2, 4,6-trioxatriphosphinane-2, 4,6 trioxide solution (50% in dimethylformamide, 2.2 ml, 3.7 mmol) and up added to the solution with dimethylformamide, and then stirred at RT for 16 h.The reaction mixture was stirred in ethyl acetate, washed twice with water and once with aqueous saturated sodium chloride solution.The organic phase was dried with sodium sulfate and the solvent removed.The crude product was stirred with acetonitrile and suction filtered.The residue was twice purified by preparative HPLC separated (eluent: acetonitrile / water with 0.1% TFA (gradient)).The crude product was stirred with methanol and sucked.This gave 202 mg (11% d. Th.) Of the title compound.
11%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide; at 20.0℃; for 16.0h;	A solution of 4-bromo-N-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine (1500 mg, 3 mmol) and <strong>[59673-74-4]6-amino-1,2-dihydro-3H-indazole-3-one</strong> (555 mg, 24mmol) in ethyl acetate (21 ml) was treated with N, N-diisopropylethylamine (1.4 ml, 7.8 mmol). Thesuspension was treated with a 2,4, 6-tripropyl-1, 3,5,2, 4,6-trioxatriphosphinane 2, 4,6 trioxidesolution (50% in dimethylformamide, 2.2 ml, 3.7 mmol) and up added to the solution withdimethylformamide, and then stirred at RT for 16 h. The reaction mixture was stirred in ethylacetate, washed twice with water and once with sodium chloride solution. The organic phase wasdried with sodium sulfate and the solvent removed. The crude product was stirred with acetonitrileand suction filtered. The residue was twice purified by preparative HPLC separated (eluent:acetonitrile / water gradient, 0.1% TFA). The crude product was stirred with methanol and suctionfiltered. This gave 202 mg (11% theoretical value)of the title compound.
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide; at 20.0℃; for 16.0h;	Containing 4-bromo-N-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine (1500 mg, 3 have mozambican ear) and <strong>[59673-74-4]6-amino-1,2-dihydro-3H-indazol-3-one</strong> (555 mg, 24 have mozambican ear) in ethyl acetate (21 ml) solution with in N, N-diisopropyl ethylamine (1.4 ml, 7.8 have mozambican ear) blend. For the suspension 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide solution (50% in DMF in, 2.2 ml, 3.7 have mozambican ear) DMF until the blending and dissolving, and then the the mixture to the stirring the mixture at room temperature for up to 16 hours. Stirring the reaction mixture in ethyl acetate, and secondary washing with water and a saturated sodium chloride aqueous solution. The organic phase with sodium sulfate drying and removing the solvent. The crude product using acetonitrile stirring and suction filtered. The residual quality by preparative HPLC to be separated and secondary (eluents: acetonitrile/water with 0.1% trifluoro acetic acid the gradient). The crude product is used for methanol stirring and suction filtered. This generating 202 mg (theoretical value of 11%) the subject compound.

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; N,N-dimethyl-formamide; at 20.0℃;

N,N-Diisopropylethylamine is added to a solution of 4-bromo-N-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine and <strong>[59673-74-4]6-amino-1,2-dihydro-3H-indazol-3-one</strong> in ethyl acetate. A 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide solution (50% in dimethylformamide) is added to the reaction mixture, and the mixture is then stirred overnight at RT. The reaction mixture is worked up by methods known to those skilled in the art and the residue is separated by means of preparative HPLC. This gives the title compound.

Reference： [1]Patent: TW2016/5828,2016,A .Location in patent: Page/Page column 46; 47
[2]Patent: TW2016/5810,2016,A .Location in patent: Paragraph 0206
[3]Patent: TW2016/5809,2016,A .Location in patent: Page/Page column 47; 48
[4]Patent: US2016/237044,2016,A1 .Location in patent: Paragraph 0548-0549

3
[ 59673-74-4 ]
(2S)-2-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-[2'-chloro-4'-(isopropylcarbamoyl)biphenyl-4-yl]propanoic acid [ No CAS ]
tert-butyl [trans-4-({(2_S)-3-[4'-(isopropylcarbamoyl)-2'-methylbiphenyl-4-yl]-1-oxo-1-[(3-oxo-2,3-dihydro-1H-indazol-6-yl)amino]propan-2-yl}carbamoyl)cyclohexyl]methyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With N-ethyl-N,N-diisopropylamine; In ethyl acetate; for 3.0h;Reflux;	A solution of (2S ) - 2- [(trans-4- [(tert-butoxycarbonyl) amino] methyl} cyclohexyl) carbonyl] - amino} -3- [4 '-(isopropylcarbamoyl) - 2'-methylbiphenyl-4-yl] propanoic acid (150 mg, 0:26 mmol) and 6-amino-l,2-dihydro-3 / i-indazol-3-one (53 mg, 0:28 mmol) in ethyl acetate (3 ml) was treated with N, Ndiisopropylethylamine(0:11 mL, 0.77 mmol). Then, 2,4,6-tripropyl-l, 3,5,2,4,6-trioxatriphosphinane2,4,6-trioxide solution (50% in ethyl acetate, 0:46 ml, 0.77 mmol) and refluxed for 3 h , Thereaction mixture was mixed with water, the precipitate is suctioned and dried via lyophilization.This gave 102 mg (55% d. Th.) Of the title compound.

Reference： [1]Patent: TW2016/5810,2016,A .Location in patent: Paragraph 0431

4
[ 59673-74-4 ]
ethyl 6-({(2S)-2-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-[4'-(cyclobutylcarbamoyl)-2'-methylbiphenyl-4-yl]propanoyl}amino)-1H-indol-2-carboxylate [ No CAS ]
tert-butyl [trans-4-({(2S)-3-[4'-(cyclobutylcarbamoyl)-2'-methylbiphenyl-4-yl]-1-oxo-1-[(3-oxo-2,3-dihydro-1H-indazol-6-yl)amino]propan-2-yl}carbamoyl)cyclohexyl]methyl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20.0℃;	A solution of (2S )- 2- [(ira Ae4- [(ieri-butoxycarbonyl) amino] methyl} cyclohexyl) - carbonyl] amino} -3- [4 '-(cyclobutylcarbamoyl) - 2'-methylbiphenyl-4-yl] propanoic acid (80 mg, 0:14 mmol) in DMF (1.5mL) was added 6-amino-l, 2-dihydro-3 / i-indazol-3-one (40 mg, 0:27 mmol) and N, Ndiisopropylethylamine(0.07 mL, 0:41 mmol). The solution was treated with HATU (77 mg, 0:41mmol) and then stirred overnight at RT. The solvent was removed and the residue dissolved in alittle DMSO / acetonitrile, filtered through a Millipore filter and purified by preparative HPLC(eluent: gradient of acetonitrile / water with 0.1% trifluoroacetic acid). This gave 28 mg (29% d.Th.) Of the title compound.

Reference： [1]Patent: TW2016/5810,2016,A .Location in patent: Paragraph 0477

5
[ 59673-74-4 ]
N-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-4-iodo-L-phenylalanine [ No CAS ]
N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-4-iodo-N-(3-oxo-2,3-dihydro-1H-indazol-6-yl)-L-phenylalaninamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With N-ethyl-N,N-diisopropylamine; HATU; In ethyl acetate; for 6.0h;Reflux;	N-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-4-iodo-L-phenylalanine (1.91 g, 3.6 mmol), 6-amino-l, 2-dihydro-3 -indazol-3-one (0:55 g, 3.60 mmol) and N, N- diisopropylamine (1.9 ml, 10.8 mmol)were suspended in 23 ml of ethyl acetate and 2,4,6-tripropyl-l, 3,5,2 , 4,6-trioxatriphosphinane-2,4,6-trioxide (50% in ethyl acetate, 5.73 g, 9.0 mmol). The mixture was then refluxed for 3 h,additional 6-amino-l, 2-dihydro-3 / i-indazol3-one (0.14g, 0.90 mmol), N, N-diisopropylamine (0:47ml, 2.70 mmol) and 2,4,6 added -Tripropyl1,3,5, 2,4, 6-trioxatriphosphinane-2,4,6-trioxide (50% inethyl acetate, 1:43 g, 2.25 mmol) and refluxed for another 3 h. The reaction mixture was treatedwith water, the phases were separated and the aqueous phase extracted three times with ethylacetate. The precipitated in two phases solid was suction filtered and dried under high vacuum.This gave 1:35 g (57%.

Reference： [1]Patent: TW2016/5810,2016,A .Location in patent: Paragraph 0350

6
[ 59673-74-4 ]
3-bromo-N-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine [ No CAS ]
3-bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-(3-oxo-2,3-dihydro-1H-indazol-6-yl)-L-phenylalaninamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 20.0℃; for 50.0h;Reflux;	Example 150A 3-Bromo-N-alpha-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-(3-oxo-2,3-dihydro-1H-indazol-6-yl)-L-phenylalaninamide 3-Bromo-N-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine, <strong>[59673-74-4]6-amino-1H-indazol-3(2H)-one</strong> and N,N-diisopropylethylamine are suspended in ethyl acetate, and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% in ethyl acetate) is added. The reaction mixture is then heated under reflux for 2 h and stirred at RT for a further 48 h. The reaction mixture is worked up by methods known to those skilled in the art and the residue is separated by means of preparative HPLC. This gives the title compound.

Reference： [1]Patent: US2016/244437,2016,A1 .Location in patent: Paragraph 1238; 1239

7
[ 59673-74-4 ]
tert-butyl [trans-4-({(2S)-3-[2'-methyl-5'-(morpholin-4-ylsulphonyl)biphenyl-3-yl]-1-oxo-1-[(3-oxo-2,3-dihydro-1H-indazol-6-yl)amino]propan-2-yl}carbamoyl)cyclohexyl]methyl}carbamate [ No CAS ]