[ CAS No. 885519-98-2 ] {[proInfo.proName]}

Name: 885519-98-2|3-Formyl-1H-indazole-5-carboxylic acid|97%
Brand: Ambeed
SKU: A108609
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Quality Control of [ 885519-98-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 885519-98-2 ]

SDS Specification

Alternatived Products of [ 885519-98-2 ]

Product Details of [ 885519-98-2 ]

CAS No. :	885519-98-2	MDL No. :	MFCD06656900
Formula :	C₉H₆N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MAPWHWRNFRJKFI-UHFFFAOYSA-N
M.W :	190.16	Pubchem ID :	22494877
Synonyms :

Calculated chemistry of [ 885519-98-2 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	48.44
TPSA :	83.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.88
Log Po/w (WLOGP) :	1.07
Log Po/w (MLOGP) :	0.13
Log Po/w (SILICOS-IT) :	1.51
Consensus Log Po/w :	0.72

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.92
Solubility :	2.3 mg/ml ; 0.0121 mol/l
Class :	Very soluble
Log S (Ali) :	-2.21
Solubility :	1.18 mg/ml ; 0.00619 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.24
Solubility :	1.1 mg/ml ; 0.00581 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

Safety of [ 885519-98-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 885519-98-2 ]

* 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 [ 885519-98-2 ]
Downstream synthetic route of [ 885519-98-2 ]

[ 885519-98-2 ] Synthesis Path-Upstream 1~1

1
[ 1670-81-1 ]
[ 885519-98-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With hydrogenchloride; sodium nitrite In water at 20℃; for 12 h;	i) 3-Formyl-1H-indazole-5-carboxylic acid To a mixture of indole-5-carboxylic acid (5.5 g, 0.0338 mol) in water (250 ml) was added NaNO₂ (23.5 g, 0.338 mol) and hydrochloride solution (6N, 42 ml, 0.293 mol). After 12 h at room temperature the precipitate was filtered off, washed with water (270 ml) and dried at 50° C. to yield 5.36 g 3-formyl-1H-indazole-5-carboxylic acid (0.028 mol, 83percent) which was used without further purification.

Reference： [1] Patent: US2006/142247, 2006, A1, . Location in patent: Page/Page column 39
[2] RSC Advances, 2018, vol. 8, # 24, p. 13121 - 13128
[3] Patent: WO2007/107346, 2007, A1, . Location in patent: Page/Page column 35

[ 885519-98-2 ] Synthesis Path-Downstream 1~25

1
[ 1670-81-1 ]
[ 885519-98-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With hydrogenchloride; sodium nitrite; In water; at 20℃; for 12h;	i) 3-Formyl-1H-indazole-5-carboxylic acid To a mixture of indole-5-carboxylic acid (5.5 g, 0.0338 mol) in water (250 ml) was added NaNO2 (23.5 g, 0.338 mol) and hydrochloride solution (6N, 42 ml, 0.293 mol). After 12 h at room temperature the precipitate was filtered off, washed with water (270 ml) and dried at 50 C. to yield 5.36 g 3-formyl-1H-indazole-5-carboxylic acid (0.028 mol, 83%) which was used without further purification.
	With hydrogenchloride; sodium nitrite; In water; at 20℃; for 12h;	i) S-Formyl-lK-indazole-S-carboxylic acidTo a mixture of indole-5-carboxylic acid (5.5g, 0.0338mol) in water (250ml) was added NaNO2 (23.5g, 0.338mol) and hydrochloride solution (6N, 42ml, 0.293mol). After 12h at room temperature the precipitate was filtered off, washed with water (270ml) and dried at 500C to yield 5.36g 3-formyl-lH-indazole-5-carboxylic acid (0.028mol, 83%) which was used without further purification.

Reference： [1]Patent: US2006/142247,2006,A1 .Location in patent: Page/Page column 39
[2]RSC Advances,2018,vol. 8,p. 13121 - 13128
[3]Patent: WO2007/107346,2007,A1 .Location in patent: Page/Page column 35

2
[ 885519-98-2 ]
6,7-diamino-1-ethyl-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one [ No CAS ]
[ 894083-16-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sulfur; In N,N-dimethyl-formamide; for 4.5h;Heating / reflux;	ii) 3-(5-Ethyl-7,7-dimethyl-6-oxo-3,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-1H-indazole-5-carboxylic acid; A mixture of 6,7-diamino-1-ethyl-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (1.1 g, 0.005 mol), <strong>[885519-98-2]3-formyl-1H-indazole-5-carboxylic acid</strong> (1.0 g, 0.005 mol) and sulfur (0.176 g, 0.005 mol) in DMF (25 ml) was heated under reflux for 4.5 h. After cooling to room temperature, the reaction mixture was poured into water. After stirring for 15 minutes the precipitate was filtered off, washed thoroughly with water and dried in vacuo over P2O5 to yield 1.74 g 3-(5-Ethyl-7,7-dimethyl-6-oxo-3,5,6,7-tetrahydro-imidazo[4,5-f]indol-2-yl)-1H-indazole-5-carboxylic acid (0.004 mol, 87%). MS: M=390.4 (ESI+) 1H-NMR (400 MHz, DMSO): delta (ppm)=1.21 (t, 3H), 1.34 (s, 6H), 3.79 (b, 2H), 7.04 and 7.46 (s, 1H, two tautomeric forms), 7.51 and 7.84 (s, 1H, two tautomeric forms), 7.70 (d, 1H), 8.02 (d, 1H), 9.22 and 9.24 (s, 1H, two tautomeric forms), 12.87 (br, 1H), 13.05 and 13.11 (s, 1H, two tautomeric forms), 13.82 and 13.86 (s, 1H, two tautomeric forms)

Reference： [1]Patent: US2006/142247,2006,A1 .Location in patent: Page/Page column 39

3
[ 885519-98-2 ]
[ 881693-01-2 ]
[ 894083-16-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sulfur; In N,N-dimethyl-formamide; for 4.5h;Heating / reflux;	ii) 3-(5-Ethyl-7,7-dimethyl-6-oxo-3,5,6,7-tetrahydro-imidazo[4,5-/]indol-2-yl)- lff-indazole-5-carboxylic acidA mixture of 5,6-diamino-l-ethyl-3,3-dimethyl-l,3-dihydro-indol-2-one (l.lg, 0.005mol), 3-formyl-lH-indazole-5-carboxylic acid (1.Og, 0.005mol) and sulfur (0.176g, 0.005mol) in DMF (25ml) was heated under reflux for 4.5h. After cooling to room temperature, the reaction mixture was poured into water. After stirring for 15 minutes the precipitate was filtered off, washed thoroughly with water and dried in vacuo over P2O5 to yield 1.74g 3-(5-ethyl-7,7-dimethyl-6-oxo-3,5,6,7- tetrahydro-imidazo[4,5-f]indol-2-yl)-lH-indazole-5-carboxylic acid (0.0044mol, 89%). MS: M = 390.4 (ESI+) 1H-NMR (400 MHz, DMSO): delta (ppm) = 1.21 (t, 3H), 1.34 (s, 6H), 3.79 (b, 2H), 7.04 and 7.46 (s, IH, two tautomeric forms), 7.51 and 7.84 (s, IH, two tautomeric forms), 7.70 (d, IH), 8.02 (d, IH), 9.22 and 9.24 (s, IH, two tautomeric forms), 12.87 (br, IH), 13.05 and 13.11 (s, IH, two tautomeric forms), 13.82 and 13.86 (s, IH, two tautomeric forms)

Reference： [1]Patent: WO2007/107346,2007,A1 .Location in patent: Page/Page column 35

4
[ 885519-98-2 ]
[ 95-54-5 ]
[ 485839-61-0 ]

Yield	Reaction Conditions	Operation in experiment
53%	With hydrogen sulfide; In methanol; water; N,N-dimethyl-formamide;	Step b A solution of <strong>[885519-98-2]3-formyl-1H-indazole-5-carboxylic acid</strong> (II) (1.67 g, 8.78 mmol), benzene-1,2-diamine (XVI) (1.04 g, 9.66 mmol) and sulfur (0.31 g, 9.66 mmol) in DMF was heated at 140 C. for 3 h under nitrogen. The solution was cooled and the excess DMF was evaporated under vacuum. Water was added to the residue and sonicated briefly to suspend the solids. The solids were filtered, washed with cold water and air dried at room temperature. The solids were boiled in methanol and the insoluble solids were filtered, washed with cold methanol and dried at room temperature under vacuum to get 3-(1H-benzimidazol-2-yl)-1H-indazole-5-carboxylic acid (29) as a off white solid (1.3 g, 4.67 mmol, 53% yield). 1H NMR (DMSO-d6) delta ppm 7.15-7.32 (m, 2H), 7.49-7.60 (m, 1H), 7.73 (d, J=8.85 Hz, 1H), 7.77-7.87 (m, 1H), 8.04 (dd, J=8.85, 1.32 Hz, 1H), 9.23 (s, 1H), 13.09 (s, 1H), 13.91 (br s, 1H); ESIMS found C15H10N4O2 m/z 279 (M+H).

Reference： [1]Patent: US2011/34441,2011,A1

5
[ 885519-98-2 ]
3-((hydroxyimino)methyl)-1H-indazole-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydroxylamine hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 12.0h;	3-Formyl-1H-indazole-5-carboxylic acid (500 mg, 2.63 mmol) was dissolved in DMF (13 mL). Hydroxylamine hydrochloride (550 mg, 7.89 mmol) and triethylamine (110 muL, 7.89 mmol) were added to the solution which was then stirred at 80 C. for 12 hours, followed by extraction with ethyl acetate and 1N HCl. The combined organic layer was washed with brine, dried with anhydrous Na2SO4, and then concentrated in a vacuum. The desired compound to be used in a subsequent reaction was obtained without separate purification (93% yield).1H NMR (400 MHz, DMSO-d6) delta 11.61 (s, 1H), 8.75 (s, 1H), 8.38 (s, 1H), 7.96 (d, 2H), 7.62 (d, 1H). Mass=205.17.

Reference： [1]Patent: US2017/158642,2017,A1 .Location in patent: Paragraph 0131; 0132

6
[ 885519-98-2 ]
3-(chloro(hydroxyimino)methyl)-1H-indazole-5-carboxylic acid [ No CAS ]