[ CAS No. 59673-74-4 ]

Name: 6-Amino-1H-indazol-3-ol
Brand: Ambeed
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

Product Details of [ 59673-74-4 ]

CAS No. :	59673-74-4	MDL No. :	MFCD07781650
Formula :	C₇H₇N₃O	Boiling Point :	278.947°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	149.15	Pubchem ID :	108801
Synonyms :

Computed Properties of [ 59673-74-4 ]

TPSA :Topological Polar Surface Area	67.2	H-Bond Acceptor Count :	3
XLogP3 :	0.5	H-Bond Donor Count :	3
SP3 :	0.00	Rotatable Bond Count :	0

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 ]

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 1~10

1
[ 59673-74-4 ]
4-bromo-N-[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine [ No CAS ]
4-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
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;	Example 14A 4-Bromo-N-alpha-[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-(3-oxo-2,3-dihydro-1H-indazol-6-yl)-L-phenylalaninamide N,N-Diisopropylethylamine (1.4 ml, 7.8 mmol) was added to 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-indazol-3-one</strong> (555 mg, 24 mmol) in ethyl acetate (21 ml). A 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide solution (50% in dimethylformamide, 2.2 ml, 3.7 mmol) and, until dissolution, dimethylformamide were added to the suspension, and the mixture was then stirred at RT for 16 h. The reaction mixture was stirred into ethyl acetate, and washed twice with water and once with aqueous sodium chloride solution. The organic phase was dried with sodium sulphate and the solvent was removed. The crude product was stirred with acetonitrile and filtered off with suction. The residue was separated twice by means of preparative HPLC (eluent: acetonitrile/water gradient, 0.1% TFA). The crude product was stirred with methanol and filtered off with suction. This gave 202 mg (11% of theory) of the title compound. 1H-NMR (400 MHz, DMSO-d6): delta=ppm 0.69-0.89 (m, 2H), 1.04-1.29 (m, 3H), 1.37 (s, 9H), 1.67 (m, 4H), 2.04-2.17 (m, 1H), 2.75 (m, 3H), 2.94-3.07 (m, 1H), 4.54-4.75 (m, 1H), 6.68-6.83 (m, 1H), 6.96 (dd, 1H), 7.25 (d, 2H), 7.39-7.56 (m, 3H), 7.84 (s, 1H), 8.09 (d, 1H), 10.20 (s, 1H), 11.08 (br. s, 1H). LC-MS (Method 1): Rt=1.00 min; MS (ESIpos): m/z=614 [M+H]+.

Reference： [1]Patent: US2016/280699,2016,A1.Location in patent: Paragraph 0464; 0465; 0466; 0467

2
[ 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 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; diisopropylamine; In ethyl acetate; for 6.0h;Reflux;	Example 5A N-alpha-[(trans-4-{[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-4-iodo-N-(3-oxo-2,3-dihydro-1H-indazol-6-yl)-L-phenylalaninamide N-[(trans-4-{[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-4-iodo-L-phenylalanine (1.91 g, 3.6 mmol), <strong>[59673-74-4]6-amino-1,2-dihydro-3H-indazol-3-one</strong> (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 admixed with 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% in ethyl acetate, 5.73 g, 9.0 mmol). This was followed by refluxing for 3 h, addition of further <strong>[59673-74-4]6-amino-1,2-dihydro-3H-indazol-3-one</strong> (0.14 g, 0.90 mmol), N,N-diisopropylamine (0.47 ml, 2.70 mmol) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% in ethyl acetate, 1.43 g, 2.25 mmol) and refluxing once again for 3 h. The reaction mixture was admixed with water, the phases were separated and the aqueous phase was extracted three times with ethyl acetate. The solid precipitated in the two phases was filtered off with suction and dried under high vacuum. This gave 1.35 g (57% of theory) of the title compound.

Reference： [1]Patent: US2016/280699,2016,A1.Location in patent: Paragraph 0430; 0431; 0432; 0433

3
[ 59673-74-4 ]
4-bromo-N-[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-L-phenylalanine [ No CAS ]
4-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; N,N-dimethyl-formamide; at 20.0℃;	Example 81A 4-Bromo-N-alpha-[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-(3-oxo-2,3-dihydro-1H-indazol-6-yl)-L-phenylalaninamide 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: US2016/237067,2016,A1.Location in patent: Paragraph 0715; 0716

4
[ 59673-74-4 ]
N-alpha-{[trans-4-(aminomethyl)cyclohexyl]carbonyl}-3-{6-[3-(dimethylamino)propoxy]pyridin-3-yl}-N-(3-oxo-2,3-dihydro-1H-indazol-6-yl)-L-phenylalaninamide hydrochloride [ No CAS ]