[ CAS No. 832715-99-8 ] {[proInfo.proName]}

Name: 832715-99-8|6-(tert-Butyl)nicotinic acid|95%
Brand: Ambeed
SKU: A259255
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Quality Control of [ 832715-99-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 832715-99-8 ]

SDS Specification

Alternatived Products of [ 832715-99-8 ]

Product Details of [ 832715-99-8 ]

CAS No. :	832715-99-8	MDL No. :	MFCD08059362
Formula :	C₁₀H₁₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CVGXKEVUQXTBGM-UHFFFAOYSA-N
M.W :	179.22	Pubchem ID :	21897804
Synonyms :

Calculated chemistry of [ 832715-99-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.47
TPSA :	50.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.77
Log Po/w (XLOGP3) :	2.09
Log Po/w (WLOGP) :	2.08
Log Po/w (MLOGP) :	0.17
Log Po/w (SILICOS-IT) :	1.87
Consensus Log Po/w :	1.6

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.48
Solubility :	0.597 mg/ml ; 0.00333 mol/l
Class :	Soluble
Log S (Ali) :	-2.77
Solubility :	0.302 mg/ml ; 0.00168 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.61
Solubility :	0.443 mg/ml ; 0.00247 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 832715-99-8 ]

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 [ 832715-99-8 ]

* 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 [ 832715-99-8 ]
Downstream synthetic route of [ 832715-99-8 ]

[ 832715-99-8 ] Synthesis Path-Upstream 1~3

1
[ 59-67-6 ]
[ 75-98-9 ]
[ 832715-99-8 ]

Reference： [1] Patent: WO2008/33858, 2008, A2, . Location in patent: Page/Page column 206
[2] Patent: WO2014/64131, 2014, A2, . Location in patent: Page/Page column 104; 105
[3] Patent: WO2008/33858, 2008, A2, . Location in patent: Page/Page column 206

2
[ 56029-45-9 ]
[ 832715-99-8 ]

Reference： [1] Patent: WO2005/7658, 2005, A2, . Location in patent: Page 229

3
[ 59-67-6 ]
[ 815-17-8 ]
[ 832715-99-8 ]

Yield	Reaction Conditions	Operation in experiment
4%	Stage #1: With sulfuric acid In water at 20℃; for 0.166667 h; Inert atmosphere Stage #2: at 90℃; for 2 h; Inert atmosphere	Step 1: Preparation of 6-tert-butylnicotinic acid To a suspension of nicotinic acid (2.00 g, 16.2 mmol) in water (250mL) was added concentrated sulfuric acid (1 mL, 18.8 mmol) and the mixture stirred under nitrogen to form a clear solution. Pivalic acid (1.83 g, 17.9 mmol) was added and stirring under nitrogen at ambient temperaturecontinued for 10 minutes. Silver nitrate (125 mg, 0.74 mmol) was added followed by ammonium persulfate (295 mg, 1.3 mmol), the flask wrapped in aluminum foil to exclude light and the mixture heated to 90 °C under nitrogen. After 2 hours the reaction mixture was cooled to ambient temperature and the aqueous mixture concentrated in vacuo to a colorless solid. The solid was triturated with tetrahydrofuran and filtered. The solid residue was retriturated withmethanol and filtered. Both filtrates were combined and concentrated in vacuo. The crude product was purified by reverse phase chromatography using a 85 g c-i 8 column gradient eluted from 10percent acetonitrile in water to 100percent acetonitrile. The product containing fractions were combined and concentrated in vacuo. The residue was lyophilized from water to give 6-tert- butylnicotinic acid as a colorless solid (139 mg, 4 percent).Lc/MS: m/z calculated for c10H13No2 ([M+Hjj: 180.2. Found: 180.1 (positive mode electrospray ionization).

Reference： [1] Patent: WO2014/90715, 2014, A1, . Location in patent: Page/Page column 45

[ 832715-99-8 ] Synthesis Path-Downstream 1~13

1
[ 56029-45-9 ]
[ 832715-99-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 80℃;	In a 5 mL reaction vial was placed 6-tert-butyl-nicotinonitrile (160 mg) and 1. 5 mL of conc. HCI. The mixture was heated overnight at 80C. The resulting mixture was concentrated under vacuum. The residue was purified by HPLC. H NMR (CDC13, 400 MHZ) 8 1. 49 (s, 9H), 7. 81 (d, 1H), 8.76 (m, 1H), 9. 48 (s, 1H). Exact mass calculated for DOT 179. 09, found 180. 2 (MH+).

Reference： [1]Patent: WO2005/7658,2005,A2 .Location in patent: Page 229

2
[ 59-67-6 ]
[ 75-98-9 ]
[ 832715-99-8 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium peroxydisulfate; sulfuric acid;silver nitrate; In water; at 90℃; for 3h;	Nicotinic acid (1.Og; 7.3mmol) is dissolved in a mixture of water(1OmL) and cone. H2SO4 (0.5mL) with stirring. tert-Butyl carboxylic acid is added, and the resulting crystalline slurry stirred under nitrogen. Catalytic AgNO3 and ammonium persulfate (140mg; O.lmmol) are then added, the flask wrapped in aluminum foil to shield from light and the reaction heated to 9O0C for 3 hr. The reaction is cooled to O0C, basified to pH 10 and extracted with EtOAc (4 x 5OmL). The pooled organic layers are washed with saturated sodium carbonate (2 x 5OmL) and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting oil is purified by flash chromatography over silica gel to provide 6-tert- butyl-nicotinic acid (1. Ig) as a white solid.

Reference： [1]Patent: WO2014/64131,2014,A2 .Location in patent: Page/Page column 104; 105
[2]Patent: WO2008/33858,2008,A2 .Location in patent: Page/Page column 206

3
[ 832715-99-8 ]
[ 886854-86-0 ]
[ 886854-82-6 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of [6-(3-amino-2-methyl-phenyl)-imidazo[l,2-a]pyrazin-8- yl]-(4-morpholin-4-ylmethyl-phenyl)-amine (150mg; 0.36mmol), benzotriazol-1- yloxytris(dimethylamino)phosphonium hexafluorophosphate (450mg; l.Ommol), and diisopropylethylamine (0.3mL; 1.7mmol) is dissolved in dimethylacetamide (ImL) and stirred at room temperature for 20min. 6-te/t-butyl-nicotinic acid (200mg; <n="208"/>l.lmmol) is added and the mixture is stirred at room temperature for 16hr.[00297] Water (1OmL) is added and the mixture is filtered to give 6-?err-Butyl-N-{2-methyl-3-[8-(4-morpholin-4-ylmethyl-phenylamino)-imidazo[l,2-a]pyrazin-6- yl] -phenyl} -nicotinamide as a crude tan solid (120mg). The crude solid is purified by flash chromatography over silica gel to provide the final compound as a pale cream solid (lOOmg)

Reference： [1]Patent: WO2008/33858,2008,A2 .Location in patent: Page/Page column 206-207

4
[ 832715-99-8 ]
[ 98-18-0 ]
[ 1143504-05-5 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of <strong>[832715-99-8]6-tert-butylpyridine-3-carboxylic acid</strong> (18 mg, 0.10 mmol) and HATU (38 mg, 0.10 mmol) in DMF (1 mL) was stirred at room temperature for 3 minutes. To this solution was added 3-amino-benzenesulfonamide (17 mg, 0. 10 mmol) and triethylamine (28 muL, 0.20 mmol). The reaction was stirred at room temperature for 16 h and purified by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give 6-tert-butyl-N-(3-(aminosulfonyl)phenyl)pyridine-3-carboxamide. LC/MS: m/z 334.3 (M+H)+ at 1.99 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Reference： [1]Patent: US2009/99233,2009,A1 .Location in patent: Page/Page column 53

5
[ 832715-99-8 ]
[ 1159710-60-7 ]
[ 1258968-08-9 ]

Yield	Reaction Conditions	Operation in experiment
34%	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;	To a solution of Intermediate 3 (250 mg, 0.83 mmol), tert-butylcarboxylic acid(89 mg, 0.88 mmol), <strong>[832715-99-8]6-(tert-butyl)pyridine-3-carboxylic acid</strong> (158 mg, 0.88 mmol), EDC (270 mg, 1.25 mmol) and HOBT (150 mg, 0.83 mmol) in DCM (5 mL) was added DIPEA (250 muL, 1.66 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction was quenched with water (10 mL). The organic layer was separated, dried (MgSO4), concentrated in vacuo and chromatographed (SiO2, 20: 1 EtOAc/MeOH), yielding the title compound (140 mg, 34%) as a white solid after freeze-drying with 1 : 1 MeCN-water. deltaH (d6-DMSO) 8.30 (s, IH), 7.61 (s, IH), 7.41-7.37 (m, 2H), 7.32 (d, J 8.1 Hz, IH), 7.21 (dd, J8.4, 1.4 Hz, IH), 7.07 (s, IH), 4.30-4.18 (m, IH), 3.93-3.90 (m, IH), 3.82 (d, J 11.6 Hz, IH), 3.78-3.75 (m, 4H), 3.59 (dd, J 11.7, 3.2 Hz, IH), 3.57-3.50 (m, 2H), 3.22-3.14 (m, 2H), 2.99 (s, 6H), 1.33 (s, 9H). LCMS (ES+) 463 (M+H)+.

Reference： [1]Patent: WO2010/146351,2010,A1 .Location in patent: Page/Page column 89

6
[ 832715-99-8 ]
[ 1613727-12-0 ]
[ 1613726-97-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	Step 3: Preparation of (R)-2-(3-(6-tert-butylnicotinamido)piperidin- 1 -yl)-5-(pyridin-2- ylamino)thiazole-4-carboxamide To a solution of <strong>[832715-99-8]6-tert-butylnicotinic acid</strong> (23.5 mg, 131 imol) and 2-((R)-3-amino-piperidin-1-yl)-5-(pyridin-2-ylamino)-thiazole-4-carboxylic acid amide (38 mg, 119 imol) in N,Ndimethylformamide (1 mL) was added diisopropylethylamine (35 tL, 200 imol) followed by 0- (benzotriazol- 1 -yl)-N,N,N?,N?-tetramethyluronium hexafluorophosphate (61 mg, 161 imol). After stirring at ambient temperature overnight under an atmosphere of argon the reaction was quenched by the addition of saturated aqueous ammonium chloride (2 mL), the mixture pouredinto water (5 mL) and extracted with ethyl acetate (3 x 3 mL). The combined organic extracts were washed with brine (2 x 2 mL), dried over sodium sulfate, filtered and concentrated in vacuo to a yellow solid. The crude product was purified by chromatography using a 13 g C-18 column gradient eluted from 10% acetonitrile in water up to 100% acetonitrile. The product containing fractions were combined and concentrated in vacuo and the residue lyophilized from acetonitrile / water to give (R)-2-(3-(6-tert-butylnicotinamido)piperidin- 1 -yl)-5-(pyridin-2-ylamino)thiazole- 4-carboxamide as a pale yellow solid (37.8 mg, 66 %).LC/MS: mlz calculated for C24H29N702S ([M+Hj): 480.6. Found: 480.3 (positive modeelectrospray ionization).

Reference： [1]Patent: WO2014/90715,2014,A1 .Location in patent: Page/Page column 46; 47

7
[ 59-67-6 ]
[ 815-17-8 ]
[ 832715-99-8 ]

Yield	Reaction Conditions	Operation in experiment
4%		Step 1: Preparation of 6-tert-butylnicotinic acid To a suspension of nicotinic acid (2.00 g, 16.2 mmol) in water (250mL) was added concentrated sulfuric acid (1 mL, 18.8 mmol) and the mixture stirred under nitrogen to form a clear solution. Pivalic acid (1.83 g, 17.9 mmol) was added and stirring under nitrogen at ambient temperaturecontinued for 10 minutes. Silver nitrate (125 mg, 0.74 mmol) was added followed by ammonium persulfate (295 mg, 1.3 mmol), the flask wrapped in aluminum foil to exclude light and the mixture heated to 90 C under nitrogen. After 2 hours the reaction mixture was cooled to ambient temperature and the aqueous mixture concentrated in vacuo to a colorless solid. The solid was triturated with tetrahydrofuran and filtered. The solid residue was retriturated withmethanol and filtered. Both filtrates were combined and concentrated in vacuo. The crude product was purified by reverse phase chromatography using a 85 g c-i 8 column gradient eluted from 10% acetonitrile in water to 100% acetonitrile. The product containing fractions were combined and concentrated in vacuo. The residue was lyophilized from water to give 6-tert- butylnicotinic acid as a colorless solid (139 mg, 4 %).Lc/MS: m/z calculated for c10H13No2 ([M+Hjj: 180.2. Found: 180.1 (positive mode electrospray ionization).

Reference： [1]Patent: WO2014/90715,2014,A1 .Location in patent: Page/Page column 45

8
[ 832715-99-8 ]
[ 1005786-37-7 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 70℃; for 3h;	A solution of <strong>[832715-99-8]6-(tert-butyl)nicotinic acid</strong> (1 , 1 .8 g, 10.05 mmol) in thionyl chloride (20 mL) was heated at 70 C for 3 h. The reaction mixture evaporated completely and dried to afford the title compound 6-(tert-butyl)nicotinoyl chloride (2, 1.8 g, crude) as a brownish liquid. The crude product was as such taken to next step without any purification.

Reference： [1]Patent: WO2018/119374,2018,A1 .Location in patent: Paragraph 00278

9
[ 832715-99-8 ]
(E)-2-((6-(tert-butyl)pyridin-3-yl)(hydroxy)methylene)-4-methoxy-3-oxobutanenitrile [ No CAS ]