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[ CAS No. 7418-65-7 ] {[proInfo.proName]}

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Chemical Structure| 7418-65-7
Chemical Structure| 7418-65-7
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Product Details of [ 7418-65-7 ]

CAS No. :7418-65-7 MDL No. :MFCD00234183
Formula : C6H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IASBMUIXBJNMDW-UHFFFAOYSA-N
M.W : 138.12 Pubchem ID :319979
Synonyms :

Calculated chemistry of [ 7418-65-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.6
TPSA : 76.21 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) : -6.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.17
Log Po/w (XLOGP3) : 0.25
Log Po/w (WLOGP) : 0.37
Log Po/w (MLOGP) : -1.72
Log Po/w (SILICOS-IT) : 0.03
Consensus Log Po/w : -0.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.23
Solubility : 8.1 mg/ml ; 0.0586 mol/l
Class : Very soluble
Log S (Ali) : -1.41
Solubility : 5.36 mg/ml ; 0.0388 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.01
Solubility : 13.5 mg/ml ; 0.0977 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.09

Safety of [ 7418-65-7 ]

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 [ 7418-65-7 ]

* 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 [ 7418-65-7 ]
  • Downstream synthetic route of [ 7418-65-7 ]

[ 7418-65-7 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 7418-65-7 ]
  • [ 7418-66-8 ]
YieldReaction ConditionsOperation in experiment
27%
Stage #1: With thionyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 3 h; Inert atmosphere
Stage #2: With ammonia In tetrahydrofuran; methanol; N,N-dimethyl-formamide at 20℃; for 4 h;
To a stirred solution of 4-aminopyridine-3-carboxylic acid (3 g, 0.013 mol) in THF (50 mL),SOCh (3.6 mL, 0.045 mol) and catalytic DMF (30 f-lL) were added at RT and stirred for 3 hunder argon atmosphere (TLC indicated complete consumption of the starting material). Thevolatiles were removed under reduced pressure to give the crude product which wasdissolved in THF (30 mL), cooled to 0 °C and 7 N NH3-methanol (22 mL) was added. Thereaction mixture was slowly warmed toRT and stirred for 4 h, the precipitate was filtered, thefiltrate was concentrated under reduced pressure to give the crude compound which waspurified by column chromatography (100-200 silica gel, 60 g, 10percent MeOH-10percent NH40HDCM)to provide 4-aminopyridine-3-carboxamide (475 mg, 27percent) which was used for thenext step without any purification.LCMS (ESI+ ): m/z: 138.33 [M+Ht.
Reference: [1] Patent: WO2018/125961, 2018, A1, . Location in patent: Page/Page column 98; 100
  • 2
  • [ 1078-05-3 ]
  • [ 7418-65-7 ]
Reference: [1] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272
[2] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 8, p. 2061 - 2071
[3] Patent: US2005/222141, 2005, A1, . Location in patent: Page/Page column 37
  • 3
  • [ 16135-36-7 ]
  • [ 7418-65-7 ]
YieldReaction ConditionsOperation in experiment
55% With lithium hydroxide monohydrate; water In ethanol at 20 - 80℃; for 2 h; To a stirred solution of methyl 4-aminopyridine-3-carboxylate (2 g, 13.15 mmol) in EtOHwater(120 mL, 1:1), LiOH·H20 (1.21 g, 28.80 mmol) was added at RT and heated at 80 °Cfor 2 h (TLC indicated complete consumption of starting material). The volatiles wereremoved under reduced pressure to give the crude compound which was dissolved in water(30 mL), washed with EtOAc (2 x 25 mL) to remove the non-polar impurities. The aqueouslayer was acidified with 1 N HCl till pH= 1, and extracted with EtOAc (2 x 10 mL). Thecombined organic extracts were concentrated under reduced pressure to give the cruderesidue which was crystallized from MeOH (20 mL) to obtain 4-aminopyridine-3-carboxylicacid (1 g, 55percent) as an off-white solid.LCMS (ESI+): m/z: 139.31 [M+Ht.
Reference: [1] Patent: WO2018/125961, 2018, A1, . Location in patent: Page/Page column 98; 99; 100
  • 4
  • [ 10177-29-4 ]
  • [ 7418-65-7 ]
YieldReaction ConditionsOperation in experiment
17 g With ammonia In water at 150℃; A solution of 4-chloropyridine-3-carboxylic acid (15 g, 0.095 mol) in aqueous NH3 (600 mL) was heated in a pressure vessel at 150 °C overnight. The progress of reaction was monitored by TLC. After completion of reaction, the mixture was concentrated under reduced pressure. To this reaction mixture was added toluene (2x100 mL) to obtain 4-aminopyridine-3-carboxylic acid (17 g) as a white solid.
Reference: [1] Synthesis, 1986, # 11, p. 886 - 891
[2] Patent: WO2006/57922, 2006, A2, . Location in patent: Page/Page column 36
[3] Patent: WO2006/52555, 2006, A2, . Location in patent: Page/Page column 31; 69-70
[4] Patent: WO2015/103355, 2015, A1, . Location in patent: Paragraph 0182
  • 5
  • [ 1003-73-2 ]
  • [ 7418-65-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 8, p. 2061 - 2071
[2] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272
  • 6
  • [ 1074-98-2 ]
  • [ 7418-65-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 8, p. 2061 - 2071
[2] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272
  • 7
  • [ 75-09-2 ]
  • [ 171178-34-0 ]
  • [ 7418-65-7 ]
Reference: [1] Patent: US5654307, 1997, A,
  • 8
  • [ 104915-66-4 ]
  • [ 7418-65-7 ]
Reference: [1] Journal of Organic Chemistry, 1954, vol. 19, p. 1633,1636[2] Org. Synth. Coll., 1963, vol. Vol. IV, p. 166
[3] European Journal of Medicinal Chemistry, 2000, vol. 35, # 1, p. 77 - 82
  • 9
  • [ 60770-86-7 ]
  • [ 7418-65-7 ]
Reference: [1] European Journal of Medicinal Chemistry, 2000, vol. 35, # 1, p. 77 - 82
  • 10
  • [ 24202-75-3 ]
  • [ 7418-65-7 ]
Reference: [1] Journal of Organic Chemistry, 1949, vol. 14, p. 97,101
  • 11
  • [ 67-56-1 ]
  • [ 7418-65-7 ]
  • [ 16135-36-7 ]
YieldReaction ConditionsOperation in experiment
67% Reflux; Cooling Step a): Methyl 4-aminopyridine-3-carboxylate
A little at a time, 4400 mg (31.86 mmol) of 4-aminopyridine-3-carboxylic acid are added to 12 ml of ice-cooled concentrated sulfuric acid.
70 ml of methanol are then added slowly.
The reaction mixture is stirred under reflux (oil bath temperature 75° C.) for 20 h.
The reaction solution is poured onto about 120 g of ice and neutralized with sodium carbonate.
After extraction with dichloromethane, the organic phase is dried over magnesium sulfate and filtered.
After 24 h of standing, the title compound crystallizes from the filtrate.
Yield: 3310 mg (67percent of theory)
LC-MS (Method 9): Rt=1.59 min;
MS (ESIpos): m/z=153 [M+H]+.
10.3 g at 0 - 85℃; To a solution of 4-aminopyridine-3-carboxylic acid (17 g, 0.123 mol) in MeOH (300 mL) was added H2SO4 (45 mL) dropwise at 0 °C. The reaction mixture was heated to reflux at 85 °C overnight. The progress of reaction was monitored by TLC. After completion of the reaction, the mixture was concentrated under reduced pressure to remove MeOH, residue was basified with a saturated aqueous solution of Na2C03 (400 mL), extracted with EtOAc (3x500 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford methyl 4-aminopyridine-3-carboxylate (10.3 g) as a white solid.
Reference: [1] Patent: US2010/4292, 2010, A1, . Location in patent: Page/Page column 17
[2] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 21, p. 7599 - 7612
[4] Patent: WO2014/71247, 2014, A1, . Location in patent: Paragraph 00323
[5] Patent: WO2015/103355, 2015, A1, . Location in patent: Paragraph 0183
[6] Chemical Communications, 2016, vol. 52, # 59, p. 9283 - 9286
[7] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1949 - 1956
  • 12
  • [ 7418-65-7 ]
  • [ 16952-64-0 ]
Reference: [1] Patent: US5654307, 1997, A,
  • 13
  • [ 7418-65-7 ]
  • [ 138116-34-4 ]
Reference: [1] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272
  • 14
  • [ 24424-99-5 ]
  • [ 7418-65-7 ]
  • [ 171178-34-0 ]
YieldReaction ConditionsOperation in experiment
69% With dmap In tetrahydrofuran; water at 20℃; for 3 h; Intermediate 6AH: 4- fcr<-Butoxycarbonylamino)pyridine-3-carboxylic acidTo a stirred solution of 4-aminopyridine-3-carboxylic acid (1.0 g, 7.2 mmol), Boc anhydride in THF: water (1: 1, 20mL) was added DMAP and stirred for 3 h at room temperature. To this was added ethyl acetate (25 mL) and water (25 mL). Aqueous layer was separated, extracted with ethyl acetate (25 mL). Combined organic layer was washed with brine (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to furnish 1.2 g (69percent) of 4-(ieri-butoxycarbonylamino)pyridine-3-carboxylic acid.MS (ES) m/z 239.1 (M+l).
69% With dmap In tetrahydrofuran; water at 20℃; for 3 h; To a stirred solution of 4-aminopyridine-3-carboxylic acid (1.0 g, 7.2 mmol), Boc anhydride in THF:water (1:1, 20 mL) was added DMAP and stirred for 3 h at room temperature. To this was added ethyl acetate (25 mL) and water (25 mL). Aqueous layer was separated, extracted with ethyl acetate (25 mL). Combined organic layer was washed with brine (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to furnish 1.2 g (69percent) of 4-(tert-butoxycarbonylamino)pyridine-3-carboxylic acid. [0349] MS (ES) m/z 239.1 (M+1)
Reference: [1] Patent: WO2013/42139, 2013, A1, . Location in patent: Page/Page column 80
[2] Patent: US2015/65464, 2015, A1, . Location in patent: Paragraph 0348-0349
  • 15
  • [ 593-51-1 ]
  • [ 7418-65-7 ]
  • [ 910656-00-7 ]
Reference: [1] Patent: WO2008/115369, 2008, A2, . Location in patent: Page/Page column 128-129
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