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[ CAS No. 72830-09-2 ] {[proInfo.proName]}

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Chemical Structure| 72830-09-2
Chemical Structure| 72830-09-2
Structure of 72830-09-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 72830-09-2 ]

CAS No. :72830-09-2 MDL No. :MFCD02181083
Formula : C8H11Cl2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YYRIKJFWBIEEDH-UHFFFAOYSA-N
M.W : 224.08 Pubchem ID :16216928
Synonyms :
2-(Chloromethyl)-3,4-dimethoxypyridine hydrochloride

Calculated chemistry of [ 72830-09-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.95
TPSA : 31.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.02
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 1.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.65
Solubility : 0.507 mg/ml ; 0.00226 mol/l
Class : Soluble
Log S (Ali) : -2.31
Solubility : 1.11 mg/ml ; 0.00495 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.3
Solubility : 0.112 mg/ml ; 0.000498 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 72830-09-2 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P362+P364-P403+P233-P501 UN#:3077
Hazard Statements:H302-H315-H318-H335-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 72830-09-2 ]

* 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 [ 72830-09-2 ]
  • Downstream synthetic route of [ 72830-09-2 ]

[ 72830-09-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 97963-62-7 ]
  • [ 72830-09-2 ]
  • [ 102625-64-9 ]
YieldReaction ConditionsOperation in experiment
97.5% With sodium hydroxide In water at 25 - 30℃; for 4 - 5 h; EXAMPLE 1 : PREPARATION OF 5-DIFLUOROMETHOXY-2(3,4-DIMETHOXY- PYRIDIN-2-YLMETHYL THIO)-1 H-BENZIMIDAZOLE (PANTOPRAZOLE SULFIDE) (FORMULA Ma)-USING 2.1 EQUIVALENTS OF SODIUM HYDROXIDE:Sodium hydroxide (37.4 g) and water (1000 ml) were taken into a clean and dry 4 neck round bottom flask and stirred for about 10 minutes. 5-difluoromethoxy-2- mercaptobenzimidazole (96.4 g) and 2-Chloromethyl-3, 4-dimethoxy-pyridine hydrochloride (100 g) dissolved in 500 ml of water was added slowly over about 2-3 hours at about 25-300C. The resultant reaction mixture was stirred for about 2 hours. The separated solid was filtered and washed with water (500 ml). <n="27"/>The obtained solid was again taken into a fresh round bottom flask containing water (500 ml) and stirred for about 20 minutes. The solid was filtered and suction dried for about 30 minutes. The obtained solid was dried under a vacuum of about 650 mm/Hg and a temperature of about 50 0C for 5 hours to afford 159 g (percent Yield: 97.5) of the title compound. Purity By HPLC: 99 percent.
95.3% With sodium hydroxide In methanol; water at 10 - 40℃; for 2.5 h; 10percent NaOH solution (42.5 gm in 425 ml of water) is added drop wise to a solution of 5-(difluoromethoxy)-2-mercapto benzimidazole (100.0 gm; 0.462 moles) in methanol(350.0 ml) at 10-150C. To the above solution a clear solution of 2-chloro-3, 4-dimethoxy pyridine hydrochloride (105.5 gm.0.473 moles in 525 ml of methanol) was added at 10-150C. The reaction mass was maintained at 10-15°C for 30 minutes. The temperature of the reaction mass was slowly raised to 2O0C. The reaction mass was maintained at 20-25° C for 2 hours. Further the temperature was raised to 400C and maintained at 400C. Completion of the reaction is monitored by TLC. After completion of the reaction methanol is evaporated under reduced pressure to get a residue. Chilled water (600 ml) was added to the residue and the reaction mass was extracted with methylene chloride (600 ml, 300 ml x 2). The organic layers were separated and evaporated under reduced pressure to obtain a residue. Isopropyl alcohol (50 ml) and hexane (600 ml) were added to the reaction mass. The reaction mass was cooled to 0-50C and maintained at 0-5°C for 30 minutes. The reaction mass was filtered at 0-5°C and washed with chilled hexane (100 ml). The solids were dried under vacuum at 4O0C; Dry wt-162 gm (Yield=95.3percent); HPLC Purity=99.21percent w/w.; Melting range=l 15-1170C (Lit.7mp-H5-1 18°C); MS (ESI); 368.0(M+H) +.
83% With water; sodium hydroxide In methanol at 25 - 30℃; Methanol (270 ml) was added to a solution of NaOH (41.5 gms) in water (180 ml), followed by addition of 5-difluoromethoxy-2-mercapto-1H-benzimidazole (105.2 gms). A solution of 2-chloromethyl-3,4-dimethoxy-pyridine.hydrochloride (100.3 gm in water (150 ml)) was gradually added to the reaction mixture and stirred at 25-30° C. till completion of the reaction. After completion, as monitored by TLC, the reaction mixture was filtered and the obtained solid was dried to give compound IV-A-11.Yield: 140.6 gm (83percent).1H NMR (400 MHz, CDCl3): δ 8.27 (d, J=5.6 Hz, 1H), 7.48 (d, J=8.8 Hz, 1H), 7.32 (d, J=2 Hz, 1H), 6.99 (dd, J=2.4, 8.8 Hz, 1H), 6.87 (d, J=5.6 Hz, 1H), 6.50 (t, J=74.8 Hz, 1H), 4.39 (s, 2H), 3.95 (s, 3H), 3.93 (s, 3H).ESI-MS: 368.9 (M+1).
16.6 g With sodium hydroxide In dichloromethane at 20 - 30℃; for 2 h; To the reaction flask was added 10 g of 2-chloromethyl-3,4-dimethoxypyridine hydrochloride(Compound 1), 10 g of 5-difluoromethoxy-2-mercapto-1H-benzimidazole(Compound 2), 100 ml of methylene chloride was added, and 130 g of a 10percent sodium hydroxide solution was added dropwise, and the mixture was stirred at 20 to 30 °C for 2 hours, Static separation, dichloromethane layer washed twice, each time with water 30ml,And then distilled under reduced pressure to give 16.6 g of a yellow oil (Intermediate 3);

Reference: [1] Patent: WO2008/45777, 2008, A2, . Location in patent: Page/Page column 25-26
[2] Patent: WO2009/66317, 2009, A2, . Location in patent: Page/Page column 7
[3] Patent: US2015/232467, 2015, A1, . Location in patent: Paragraph 0070-0073
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1049 - 1057
[5] Patent: WO2005/77936, 2005, A1, . Location in patent: Page/Page column 16-17
[6] Patent: WO2008/1392, 2008, A2, . Location in patent: Page/Page column 17-20
[7] Patent: WO2009/10937, 2009, A1, . Location in patent: Page/Page column 11
[8] Patent: US2010/210847, 2010, A1, . Location in patent: Page/Page column 4
[9] Patent: WO2006/49486, 2006, A1, . Location in patent: Page/Page column 13; 14
[10] Organic Process Research and Development, 2004, vol. 8, # 2, p. 266 - 270
[11] Chemistry Letters, 2016, vol. 45, # 2, p. 110 - 112
[12] Patent: CN104262326, 2016, B, . Location in patent: Paragraph 0034; 0035
[13] Patent: CN105111187, 2017, B, . Location in patent: Paragraph 0012; 0027; 0028
[14] Patent: CN108341800, 2018, A, . Location in patent: Paragraph 0006; 0009
  • 2
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Reference: [1] Patent: WO2007/86077, 2007, A2, . Location in patent: Page/Page column 8-9
  • 3
  • [ 97963-62-7 ]
  • [ 72830-09-2 ]
  • [ 138786-67-1 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With sodium hydroxide In dichloromethane; water at 25 - 30℃; for 12 h;
Stage #2: With sodium hydroxide; sodium hypochlorite In dichloromethane; water at 0 - 8℃; for 6 h;
2-Chloromethyl-3,4-dimethoxy pyridine hydrochloride (50 gms), 2-mercapto-5-difluoromethoxy15 benzimidazole (50 gms) and Tetra butyl ammonium bromide (2 gms) were added under stirring to dichloromethane (300 ml) followed by solution of sodium hydroxide ( 37.5 gms ) in 120 ml water.The contents were then stirred at 25 - 30° C for about 12 hours. After reaction completion, the dichloromethane layer was separated, then the aqueous layer was extracted with dichloromethane(60 ml) twice. The organic layers were combined together, water washed and distilled to about20 250ml and cooled to 00C. 3.5percent aqueous sodium hypochlorite solution (464 g ) having a sodium hydroxide content of 2.2percent was added to the reaction mass, which was maintained at 5 - 80C for about 6 hours. After completion of the reaction; the reaction mass was further cooled to 0 to 5°C.The resulting solid was then filtered and washed with cold acetone (about 100ml ) and dried under vacuum at 35-400C to give pantoprazole sodium (75 gms, 83percent) of purity greater than 99.5percent.
Reference: [1] Patent: WO2006/64249, 2006, A2, . Location in patent: Page/Page column 8; 10
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