Home Cart 0 Sign in  
X

[ CAS No. 21901-41-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 21901-41-7
Chemical Structure| 21901-41-7
Chemical Structure| 21901-41-7
Structure of 21901-41-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 21901-41-7 ]

Related Doc. of [ 21901-41-7 ]

Alternatived Products of [ 21901-41-7 ]
Product Citations

Product Details of [ 21901-41-7 ]

CAS No. :21901-41-7 MDL No. :MFCD00010690
Formula : C6H6N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :AIEHUZHKFUNHCJ-UHFFFAOYSA-N
M.W : 154.12 Pubchem ID :345371
Synonyms :

Calculated chemistry of [ 21901-41-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.05
TPSA : 78.94 Ų

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) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.16
Log Po/w (XLOGP3) : 1.02
Log Po/w (WLOGP) : 1.0
Log Po/w (MLOGP) : 0.25
Log Po/w (SILICOS-IT) : -0.81
Consensus Log Po/w : 0.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.78
Solubility : 2.58 mg/ml ; 0.0168 mol/l
Class : Very soluble
Log S (Ali) : -2.27
Solubility : 0.833 mg/ml ; 0.0054 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.2
Solubility : 9.66 mg/ml ; 0.0627 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 21901-41-7 ]

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 [ 21901-41-7 ]

* 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 [ 21901-41-7 ]
  • Downstream synthetic route of [ 21901-41-7 ]

[ 21901-41-7 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 21901-41-7 ]
  • [ 5334-39-4 ]
Reference: [1] Russian Journal of Organic Chemistry, 2008, vol. 44, # 8, p. 1205 - 1210
  • 2
  • [ 21901-41-7 ]
  • [ 399-88-2 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
  • 3
  • [ 21901-41-7 ]
  • [ 3430-27-1 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
  • 4
  • [ 21901-41-7 ]
  • [ 23056-33-9 ]
YieldReaction ConditionsOperation in experiment
86% at 150℃; for 2 h; Example 1223-((5-Amino-4-methylpyridin-2-yl)ethynyl)-7,7-dimethyl-7,8-dihydroquinolin-5(6H)- one [00334]A mixture of 4-methyl-5-nitropyridin-2-ol (500 mg, 3.24 mmol), POCI3 (0.5 mL) and PCI5 (200 mg) is stirred at 150 °C for 2 h, cooled down to r.t., poured onto ice and extracted with DCM (3x20 mL). The combined organic phases are washed with water to reach pH 7, dried over Na2S04 and concentrated at reduced pressure. The obtained residue is dried at reduced pressure to give crude 2-chloro-4-methyl-5-nitropyridine (480 mg, 86percent).[00335]According to General Procedure 2, 3-ethynyl-7,7-dimethyl-7,8-dihydroquinolin- 5(6/-/)-one (199 mg, 1 .00 mmol) is reacted with 2-chloro-4-methyl-5-nitropyridine (172 mg, 1.00 mmol) in the presence of PdCI2(PPh3)2 (42 mg, 0.06 mmol), P(f-Bu)3 (16 mg, 0.08 mmol), and TEA (1 .5 mL) in DMF (3 mL) at 100 °C for 3 h. The crude product is purified by column chromatography (silica gel) to give the intermediate product 7,7- dimethyl-3-((4-methyl-5-nitropyridin-2-yl)ethynyl)-7,8-dihydroquinolin-5(6/-/)-one (1 15 mg, 34percent).[00336]A mixture of 7,7-dimethyl-3-((4-methyl-5-nitropyridin-2-yl)ethynyl)-7,8- dihydroquinolin-5(6/-/)-one (1 14 mg, 0.34 mmol) and SnCI2*2H20 (380 mg, 1 .70 mmol) in EtOH (10 mL) is stirred at reflux for 6 h, cooled to r.t., poured onto ice, treated with saturated aqueous NaHCOs solution to reach pH 7-8, and extracted with EtOAc (3x30 mL). The combined organic phases are dried over Na2S04 and concentrated at reduced pressure. The obtained residue is purified by washing with hexane and acetonitrile to provide the title compound (60 mg, 58percent).1H NMR (De-DMSO), δΗ, 1 .07 (s, 6H), 2.08 (s, 3H), 2.60 (s, 2H), 3.02 (s, 2H), 5.51 (s, 2H), 7.23 (s, 1 H), 7.90 (s, 1 H), 8.17 (s, 1 H), 8.80 (s, 1 H).LC/MS (M+H)+ = 306
Reference: [1] Patent: WO2012/52451, 2012, A1, . Location in patent: Page/Page column 117-118
[2] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
[3] Journal of the Chemical Society, 1954, p. 1190,1192
[4] Journal of the Chemical Society, 1954, p. 2448,2455
[5] Patent: WO2007/53394, 2007, A1, . Location in patent: Page/Page column 12
[6] Patent: EP2366691, 2011, A1, . Location in patent: Page/Page column 13
[7] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 143 - 157
[8] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 21, p. 5229 - 5233
[9] Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 1, p. 66 - 81
[10] Patent: WO2008/101682, 2008, A2, . Location in patent: Page/Page column 61
  • 5
  • [ 21901-41-7 ]
  • [ 23056-33-9 ]
  • [ 17288-53-8 ]
YieldReaction ConditionsOperation in experiment
95% With thionyl chloride In <i>N</i>-methyl-acetamide; dichloromethane; toluene EXAMPLE 12
5-Methoxypyrrolo[2,3-c]pyridine (Compound 9)
A mixture of 4-methyl-5-nitro-1H-pyridine-2-one (5.00 g, 32.44 mmol), thionyl chloride (20 ml), and two drops of dimethylformamide was heated atreflux under nitrogen for 52 hours.
The resultant orange colored solution was evaporated under reduced pressure, and a small amount of anhydrous toluene was added and then removed via evaporation under reduced pressure to remove traces of thionyl chloride.
The residual oil then passed througha silica gel filter (dried at 150° C. under vacuum overnight, approximately 100 g) followed by methylene chloride (1 1).
This filtrate was evaporated under reduced pressure to afford 2-chloro-4-methyl-5-nitropyridine (5.30 g, 30.71 mmol, 95percent) as an orange oil, which crystallized below 0° C.; IR (CHCl3) 1605, 1550, 1520, 1450, 1360, 1345 cm-1; 1 H NMR (CDCl3) δ 9.03 (s, 1H), 7.83 (s, 1H), 2.60 (s, 3H); LRMS (m/z, relative intensity) 174 (25), 173 (19), 172 (M+, 68), 157 (74), 155 (100), 128 (27), 101 (47), 100(55], 99 (74), 90 (43), 75 (36).
Reference: [1] Patent: US5051412, 1991, A,
  • 6
  • [ 21901-40-6 ]
  • [ 21901-41-7 ]
YieldReaction ConditionsOperation in experiment
67.2% at -5 - 0℃; for 3.16667 h; Weigh the starting material 2-amino-4-methyl-5-nitropyridine 23 (10 g) in a 250 ml round bottom flask and 70 ml of concentrated H2SO4Stirring dissolved, until the raw material is completely dissolved, the reaction flask placed in -5 low temperature cold bath, from the constant pressure low liquid funnel slowly dropping pre-configured NaNO2(6.76g) solution, resulting in a large number of bubbles, to avoid the temperature rise too fast to keep the whole process does not exceed the temperature of 0 , with the reaction, the reaction bottle gradually precipitated solid, drop Bi, stirring 10min reaction liquid into orange The solution was clarified and the reaction was continued at 0 ° C.TLC monitoring showed complete response after 3 h, stop the reaction.The reaction solution was poured into a beaker containing about 300 ml of water to precipitate a large amount of a yellow solid. After crystallization at room temperature for 3 hours, the solid was collected by filtration and dried under an infrared lamp to give 6.72 g of a yellow solid in 67.2percent yield.
63.7% at 0 - 20℃; for 2 h; Synthesis of the compound 31 The compound 30 (17.4 g, 0.114 mol) was added into 300 mL of water, a concentrated sulphuric acid (30 mL) was slowly added with agitation and cooled to 0°C in an ice bath. Sodium nitrite (17.5 g, 0.254 mol) was dissolved in 35 mL of water and added slowly beneath the reaction liquid surface of the reaction system via a long stem funnel. The reaction was run at room temperature for 2 h and boiled up until the reaction ends which was marked by no further brown gas was emitted. The reaction liquid was poured into broken ice, filtered, and dried to obtain 11.15g of the compound 31 with a yield of 63.7percent. The melting point is 187.3-188.9°C (ethanol) (M.P. 186°C was reported in the reference)[J. Chem. Soc.. 1954, 2248 -2451].
Reference: [1] Patent: CN105906621, 2016, A, . Location in patent: Paragraph 0045
[2] Patent: EP2366691, 2011, A1, . Location in patent: Page/Page column 13
[3] Journal of the Chemical Society, 1954, p. 2448,2455
[4] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
[5] Patent: WO2007/53394, 2007, A1, . Location in patent: Page/Page column 12
[6] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 143 - 157
[7] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 21, p. 5229 - 5233
[8] Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 1, p. 66 - 81
  • 7
  • [ 6635-90-1 ]
  • [ 21901-41-7 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogen bromide In acetic acid at 0 - 60℃; for 2 h; The product of step 1 (0.13 g, 0.77 mmol) was dissolved in a 0°C solution of HBr in acetic acid (33percent w/w, 5ml) and then stirred at 60°C for 2 h, cooled to room temperature and poured into diethyl ether (10ml). The crystalline precipitate that was filtered, washed with ether and dried 0.155 g (86percent) of 4-methyl-5-nitro-pyridin-2-ol.
Reference: [1] Patent: EP1894924, 2008, A1, . Location in patent: Page/Page column 33
  • 8
  • [ 695-34-1 ]
  • [ 21901-41-7 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 2448,2455
[2] Patent: EP2366691, 2011, A1,
[3] Patent: CN105906621, 2016, A,
  • 9
  • [ 695-34-1 ]
  • [ 21901-41-7 ]
  • [ 21901-18-8 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
  • 10
  • [ 695-34-1 ]
  • [ 21901-41-7 ]
  • [ 21901-18-8 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
  • 11
  • [ 21901-41-7 ]
  • [ 393-53-3 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1729,1731
  • 12
  • [ 21901-41-7 ]
  • [ 23056-33-9 ]
  • [ 17288-53-8 ]
YieldReaction ConditionsOperation in experiment
95% With thionyl chloride In <i>N</i>-methyl-acetamide; dichloromethane; toluene EXAMPLE 12
5-Methoxypyrrolo[2,3-c]pyridine (Compound 9)
A mixture of 4-methyl-5-nitro-1H-pyridine-2-one (5.00 g, 32.44 mmol), thionyl chloride (20 ml), and two drops of dimethylformamide was heated atreflux under nitrogen for 52 hours.
The resultant orange colored solution was evaporated under reduced pressure, and a small amount of anhydrous toluene was added and then removed via evaporation under reduced pressure to remove traces of thionyl chloride.
The residual oil then passed througha silica gel filter (dried at 150° C. under vacuum overnight, approximately 100 g) followed by methylene chloride (1 1).
This filtrate was evaporated under reduced pressure to afford 2-chloro-4-methyl-5-nitropyridine (5.30 g, 30.71 mmol, 95percent) as an orange oil, which crystallized below 0° C.; IR (CHCl3) 1605, 1550, 1520, 1450, 1360, 1345 cm-1; 1 H NMR (CDCl3) δ 9.03 (s, 1H), 7.83 (s, 1H), 2.60 (s, 3H); LRMS (m/z, relative intensity) 174 (25), 173 (19), 172 (M+, 68), 157 (74), 155 (100), 128 (27), 101 (47), 100(55], 99 (74), 90 (43), 75 (36).
Reference: [1] Patent: US5051412, 1991, A,
  • 13
  • [ 21901-41-7 ]
  • [ 66909-38-4 ]
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 143 - 157
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 21, p. 5229 - 5233
[3] Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 1, p. 66 - 81
  • 14
  • [ 21901-41-7 ]
  • [ 76006-08-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 143 - 157
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 21, p. 5229 - 5233
[3] Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 1, p. 66 - 81
  • 15
  • [ 21901-41-7 ]
  • [ 267875-30-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 5, p. 795 - 798
  • 16
  • [ 21901-41-7 ]
  • [ 800401-70-1 ]
Reference: [1] Patent: WO2004/104001, 2004, A2,
[2] Patent: WO2004/104001, 2004, A2,
  • 17
  • [ 21901-41-7 ]
  • [ 907545-47-5 ]
Reference: [1] Patent: EP2366691, 2011, A1,
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 21901-41-7 ]

Alcohols

Chemical Structure| 211555-30-5

[ 211555-30-5 ]

6-Amino-5-nitropyridin-2-ol

Similarity: 0.78

Chemical Structure| 99479-77-3

[ 99479-77-3 ]

4-Amino-5-nitro-2-pyridinol

Similarity: 0.77

Chemical Structure| 15862-33-6

[ 15862-33-6 ]

3-Bromo-2-hydroxy-5-nitropyridine

Similarity: 0.73

Chemical Structure| 25391-58-6

[ 25391-58-6 ]

3-Iodo-5-nitropyridin-2-ol

Similarity: 0.72

Chemical Structure| 36625-57-7

[ 36625-57-7 ]

(5-Nitropyridin-2-yl)methanol

Similarity: 0.71

Nitroes

Chemical Structure| 5418-51-9

[ 5418-51-9 ]

2-Hydroxy-5-nitropyridine

Similarity: 0.87

Chemical Structure| 1074-99-3

[ 1074-99-3 ]

2,4-Dimethyl-5-nitropyridine

Similarity: 0.82

Chemical Structure| 153813-70-8

[ 153813-70-8 ]

3-Nitroisonicotinaldehyde

Similarity: 0.81

Chemical Structure| 5446-92-4

[ 5446-92-4 ]

2-Methoxy-5-nitropyridine

Similarity: 0.81

Chemical Structure| 21901-40-6

[ 21901-40-6 ]

4-Methyl-5-nitropyridin-2-amine

Similarity: 0.79

Related Parent Nucleus of
[ 21901-41-7 ]

Pyridines

Chemical Structure| 5418-51-9

[ 5418-51-9 ]

2-Hydroxy-5-nitropyridine

Similarity: 0.87

Chemical Structure| 1074-99-3

[ 1074-99-3 ]

2,4-Dimethyl-5-nitropyridine

Similarity: 0.82

Chemical Structure| 153813-70-8

[ 153813-70-8 ]

3-Nitroisonicotinaldehyde

Similarity: 0.81

Chemical Structure| 5446-92-4

[ 5446-92-4 ]

2-Methoxy-5-nitropyridine

Similarity: 0.81

Chemical Structure| 21901-40-6

[ 21901-40-6 ]

4-Methyl-5-nitropyridin-2-amine

Similarity: 0.79