Home Cart 0 Sign in  

[ CAS No. 106092-09-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 106092-09-5
Chemical Structure| 106092-09-5
Structure of 106092-09-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 106092-09-5 ]

Related Doc. of [ 106092-09-5 ]

Alternatived Products of [ 106092-09-5 ]

Product Details of [ 106092-09-5 ]

CAS No. :106092-09-5 MDL No. :MFCD07368003
Formula : C7H11N3S Boiling Point : -
Linear Structure Formula :- InChI Key :DRRYZHHKWSHHFT-BYPYZUCNSA-N
M.W :169.25 Pubchem ID :11521153
Synonyms :

Calculated chemistry of [ 106092-09-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.57
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.66
TPSA : 93.17 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) : -7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 0.45
Log Po/w (WLOGP) : 0.55
Log Po/w (MLOGP) : 0.06
Log Po/w (SILICOS-IT) : 1.64
Consensus Log Po/w : 0.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.51
Solubility : 5.24 mg/ml ; 0.031 mol/l
Class : Very soluble
Log S (Ali) : -1.97
Solubility : 1.79 mg/ml ; 0.0106 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.45
Solubility : 6.03 mg/ml ; 0.0356 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.16

Safety of [ 106092-09-5 ]

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 [ 106092-09-5 ]

* 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 [ 106092-09-5 ]
  • Downstream synthetic route of [ 106092-09-5 ]

[ 106092-09-5 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 106006-83-1 ]
  • [ 106092-11-9 ]
  • [ 106092-09-5 ]
Reference: [1] Bioorg. Med. Chem. Lett., 2004, vol. 14, # 12, p. 3251 - 3256
[2] Patent: WO2006/12276, 2006, A1, . Location in patent: Page/Page column 16-17
  • 2
  • [ 106006-83-1 ]
  • [ 106092-09-5 ]
YieldReaction ConditionsOperation in experiment
27.9%
Stage #1: With L-Tartaric acid In water at 75℃; for 1 h;
Stage #2: With hydrogenchloride In water
33.8 g of 2,6-diamino-4,5,6,7-tetrahydrobenzothiazole, 500 mL of water was added, and 30.0 g of L-(+)-tartaric acid was further added, and the mixture was heated to 75 ° C and stirred for 1 hour. Cool to room temperature and stir for 24 hours, filter, wash with water and vacuum dry (55 ° C ~ 65 ° C, -0.01 MPa ~ -0.1 MPa) for 8-12 hours to obtain (S)-2,6-diamino-4,5,6 , 7-tetrahydrobenzothiazole di L-(+)-tartrate crude 35.1 g, enantiomeric content 2.53percent (chiral-HPLC). The whole batch of (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole di L-(+)-tartrate was added to 500 mL of water and heated to 75 ° C for 1 hour. Cool down to the roomStir for 24 hours, filter, wash with water and dry in vacuum (55 ° C 65 ° C, -0.01 MPa ~ -0.1 MPa) for 8-12 hours to obtain (S)-2,6-diamino-4,5,6,7- Tetrahydrobenzothiazole di L-(+)-tartrate 26.9 g, enantiomeric content 0.08percent. Add the whole batch of (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole di L-(+)-tartrate to 200 mL of water and 40 mL of hydrochloric acid, stir to dissolve, add 35 drops. The aqueous solution of potassium hydroxide (the mass percentage refers to the mass of potassium hydroxide as a percentage of the total mass of the potassium hydroxide aqueous solution) is neutralized, cooled to room temperature and stirred for 1 hour, filtered, washed with water and dried in vacuo (55 ° C ~ 65 ° C, -0.01 MPa ~ -0.1 MPa) 8-12 hours to obtain (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole 9.43 g, yield 27.9percent, The enantiomeric content was 0.08percent.
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5501 - 5521
[2] Patent: CN108084115, 2018, A, . Location in patent: Paragraph 0086; 0089
[3] Journal of Medicinal Chemistry, 1987, vol. 30, # 3, p. 494 - 498
[4] Patent: WO2011/21214, 2011, A2,
[5] Investigational New Drugs, 2010, vol. 28, # 4, p. 454 - 465
  • 3
  • [ 873431-80-2 ]
  • [ 106092-09-5 ]
Reference: [1] Patent: WO2008/86047, 2008, A1, . Location in patent: Page/Page column 142-144
[2] Patent: WO2008/41240, 2008, A1, . Location in patent: Page/Page column 18
[3] Patent: WO2011/21214, 2011, A2, . Location in patent: Page/Page column 10; 12
  • 4
  • [ 1315483-31-8 ]
  • [ 106092-09-5 ]
YieldReaction ConditionsOperation in experiment
1.05% With hydrogenchloride; potassium hydroxide In water at 0 - 5℃; for 1 - 2 h; 100gm(0.3134mole) (S)-Tartarate salt of 2,6-diamino-4,5,6,7-tetrahydro benzothiazolewas added to 79.69ml water. Cool the reaction mass to 0-5°C with stirring. Add71.99ml cone. HC1 slowly and drop wise. Then add 240ml 85percent KOH solution drop wiseto reaction mass. Maintain temperature 0-5°C during complete addition. Stir reactionmass for l-2hrs at 0-5°C. Filter the product.YIELD :56gm(1.05percent)PURITY: 99.6percent
Reference: [1] Patent: WO2006/3677, 2006, A1, . Location in patent: Page/Page column 10; 18
  • 5
  • [ 27514-08-5 ]
  • [ 17356-08-0 ]
  • [ 106092-09-5 ]
Reference: [1] Patent: CN104496936, 2017, B, . Location in patent: Paragraph 0057; 0059-0062
  • 6
  • [ 27514-08-5 ]
  • [ 106092-09-5 ]
Reference: [1] Patent: WO2011/21214, 2011, A2,
[2] Investigational New Drugs, 2010, vol. 28, # 4, p. 454 - 465
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5501 - 5521
[4] Patent: CN108084115, 2018, A,
  • 7
  • [ 106006-80-8 ]
  • [ 106092-09-5 ]
Reference: [1] Investigational New Drugs, 2010, vol. 28, # 4, p. 454 - 465
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5501 - 5521
[3] Patent: CN108084115, 2018, A,
  • 8
  • [ 687639-03-8 ]
  • [ 106092-09-5 ]
Reference: [1] Investigational New Drugs, 2010, vol. 28, # 4, p. 454 - 465
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5501 - 5521
  • 9
  • [ 104617-50-7 ]
  • [ 106092-09-5 ]
Reference: [1] Patent: WO2011/21214, 2011, A2,
  • 10
  • [ 113030-24-3 ]
  • [ 106092-09-5 ]
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 16-17, p. 1239 - 1245
  • 11
  • [ 4746-97-8 ]
  • [ 106092-09-5 ]
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 16-17, p. 1239 - 1245
  • 12
  • [ 144810-01-5 ]
  • [ 106092-09-5 ]
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 16-17, p. 1239 - 1245
  • 13
  • [ 159015-33-5 ]
  • [ 106092-09-5 ]
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 16-17, p. 1239 - 1245
  • 14
  • [ 404892-23-5 ]
  • [ 106092-09-5 ]
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 16-17, p. 1239 - 1245
  • 15
  • [ 106006-83-1 ]
  • [ 106092-11-9 ]
  • [ 106092-09-5 ]
Reference: [1] Bioorg. Med. Chem. Lett., 2004, vol. 14, # 12, p. 3251 - 3256
[2] Patent: WO2006/12276, 2006, A1, . Location in patent: Page/Page column 16-17
  • 16
  • [ 123-38-6 ]
  • [ 106092-09-5 ]
  • [ 104632-26-0 ]
YieldReaction ConditionsOperation in experiment
80.1%
Stage #1: With sulfuric acid In methanol at 0℃; for 1.5 h;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 25℃; for 1.83333 - 1.91667 h;
50gm (0.2958mole) (6S)-4,5,6,7-tetrahydro-l,3-benzthiazole-2,6-diamuie was dissolved propionaldehyde and 1.3gm cone, sulfuric acid (0.044mole). After stirring to 90 minutesadd 16.78gm (0.443 5mole) sodium borohydride. Allow increasing temperature of massto 25°C. After one hrs add second lot of 17.22gm (0.2970mole) propionaldehyde andagitate for 10-15mins. Then add 11.19gm (0.2957mole) sodium borohydride and stirr for40mins. Add 150-ml brine solution and stirr for SOmins. Distill off solvent underreduced pressure at 40°C. Add 500ml ethyl acetate and water, Separate organic phase,dry it and distilled off ethyl acetate under reduced pressure at 40°C. Residue iscrystallizing in Acetonitrile.YIELD: 34.75 gm (80.1percent)PURITY: 99.5percent^NMRinDMSO: 1.14ppm(d, 3H) C(3'); 4.12 ppm (m,lH) C(2'); 3.0 ppm (m,lH) C(l'); 3.54 ppm (m,lH) C(6); 3.10 ppm (m,2H) C(7); 2.34 ppm (m, 2H) C(3); 2.09 ppm (m,2H) C(4)13C NMR in DMSO: C(4) 23.2 ppm , C(5) 20.9 ppm , C(7) 24.69 ppm.,. .euro.(6) 52.65 ppm, C(1')51.51,C(2.)62.30, C(3')21.02ppm; thiazolering C(2') 168.7ppm; C(4') 132.8 ppm, C(5') 110.83 ppm
69%
Stage #1: at 5℃; for 0.25 h;
Stage #2: With sodium tris(acetoxy)borohydride In methanol at 5 - 25℃; for 0.583333 h;
A reaction vessel equipped with a magnetic stirrer and a thermometer was charged with (S)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole (5.0 g, 0.0296 mole) and methanol (100 ml) and the solution was cooled to 5° C. under constant stirring.
A solution of propionaldehyde (2.7 ml) in methanol (10 ml) was added while maintaining the inner temperature at 5° C.
The reaction mixture was stirred at this temperature for 15 minutes.
Sodium triacetoxyborohydride (8.75 g, 0.0413 mole) was added in 4-5 portions while maintaining the temperature at 5° C.
Stirring was continued at 5° C. for 5 minutes and the mixture was allowed to warm to 25° C. during about 30 minutes.
A mixture of water (100 ml) and 32percent HCl solution (30 ml) was added to the reaction mixture to afford a suspension.
The reaction mixture was evaporated to dryness under reduced pressure keeping the bath temperature at less then 50° C. Water (20 ml) and ethyl acetate (60 ml) were added to afford a two-phase system, and 45percent aqueous sodium hydroxide solution (4.5 ml) was added.
The layers were separated and the upper organic layer was washed with water (2*10 ml).
The ethyl acetate solution was evaporated to dryness keeping the bath temperature at less than 50° C. to afford an oily residue.
Ethyl acetate (7 ml) was added to the oily residue and the suspension thus formed was stirred at 50° C. for 15 minutes.
The mixture was allowed to cool to 25° C. and stirred at this temperature for 1 hour.
Then, the mixture was cooled down to 5° C. and stirred at this temperature for 1 hour.
The precipitate thus formed was filtered, washed with cold ethyl acetate and dried at 60° C. to yield 4.3 g (69percent) of pramipexole base.
Reference: [1] Patent: WO2006/3677, 2006, A1, . Location in patent: Page/Page column 10; 18-19
[2] Patent: US2006/148866, 2006, A1, . Location in patent: Page/Page column 2; 4
[3] Patent: WO2015/155704, 2015, A1, . Location in patent: Page/Page column 15
  • 17
  • [ 540-54-5 ]
  • [ 106092-09-5 ]
  • [ 104632-26-0 ]
YieldReaction ConditionsOperation in experiment
95% With NPs-Fe3O4(at)SiO2(at)[PrMIM]PW In acetonitrile at 50℃; Aniline (0.47 g, 5 mmol, 1 equiv.) and propyl chloride (0.39 g, 5 mmol, 1 equiv.) were added to a mixture of catalyst MSPW (5 mol percent) in acetonitrile (5 mL) in a 10 mL flask and refluxed for 1 h. The progress of the reaction was checked by TLC. After the completion of the reaction, the solid catalyst was removed with a magnet and the solvent was evaporated. The residue was added to dichloromethane : sodium hydroxide (33 percent) (1:1) biphasic system. The organic layer was then evaporated and the precipitate was dried to afford N-propylaniline, as a viscous yellow oil (0.64 g, 95 percent). As presented in Table 2, this reaction was performed with 2,6-diamino-4,5,6,7-tetrahydrobenzothiazole and sulfanilamide in the presence of MSPW similar to the methods described in the previous sections. Briefly, 2,6-diamino-4,5,6,7-tetrahydrobenzothiazole (0.85 g, 5 mmol, 1 equiv.) and propyl chloride (0.39 g, 5 mmol, 1 equiv.) were added to a mixture of catalyst MSPW (5 mol percent) in acetonitrile (5 mL) and refluxed for 1 h. After catalyst recycling and work-up the reaction, N6-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine, pramipexole free base (m3, API), was obtained as a light yellow solid (0.99 g, 95 percent).
Reference: [1] Research on Chemical Intermediates, 2017, vol. 43, # 3, p. 1957 - 1968
  • 18
  • [ 123-62-6 ]
  • [ 106092-09-5 ]
  • [ 104632-26-0 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With triethylamine In tetrahydrofuran at -10 - 0℃; for 2 h;
Stage #2: at 50 - 55℃; for 1 h;
(S)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole 6.8 g and 4.4 g of triethylamine were added to 60 mL of tetrahydrofuran, and 5.8 g of propionic anhydride was added at -10 ° C to 0 ° C. Stir at -10 ° C ~ 0 ° C for 2 hours. 40 mL of water was added, and concentrated in vacuo (45 ° C - 55 ° C, -0.085 MPa - -0.1 MPa) to remove tetrahydrofuran, 40 mL of ethyl acetate was added, and the mixture was stirred and allowed to stand for separation. The aqueous phase was extracted twice with ethyl acetate (40 mL). The phase percentage is 10percent aqueous solution of sodium hydrogencarbonate (the mass percentage refers to the mass of sodium hydrogencarbonate as a percentage of the total mass of the aqueous solution of sodium hydrogencarbonate) and the mass percentage is 15percent.The brine (the mass percentage refers to the mass of sodium chloride as a percentage of the total mass of the brine solution) is washed and dried over anhydrous sodium sulfate. Filtration, cooling and concentration in vacuo to remove most of the solvent (35 ° C ~ 45 ° C, -0.05 MPa ~ -0.1 MPa), added100 mL of tetrahydrofuran, a solution of 1 mol/L borane tetrahydrofuran complex in tetrahydrofuran (the content of the substance refers to the ratio of the amount of borane to the total volume of the solution) 180 mL, and heated to 50 ° C to 55 ° C to stir 1 hour. Add water50mL, concentrated in vacuo (45 ° C ~ 55 ° C, -0.085MPa ~ -0.1MPa) to remove tetrahydrofuran, add 50mL of ethyl acetate, stir and then layer, the aqueous phase was extracted twice with 50mL of ethyl acetate, combined with organic phase 10percent by mass sodium bicarbonateAqueous solution (the mass percentage refers to the mass of sodium bicarbonate as a percentage of the total mass of the aqueous solution of sodium bicarbonate) and the mass percentage of 15percent saline (the mass percentage refers to sodium chloride) Quality accounts for the total mass of saline solutionThe percentage is washed and dried over anhydrous sodium sulfate. Filtration, cooling and concentration in vacuo to remove most of the solvent (35 ° C ~ 45 ° C, -0.05 MPa ~ -0.1 MPa), add acetone 40mL, stir at room temperature for 2 hours, filter, acetone wash, and vacuum drying (45 ° C55° C., −0.01 MPa to −0.1 MPa) 8.12 g of pramipexole II was obtained in 8 to 12 hours, the yield was 85.0percent, and the enantiomeric content was 0.08percent.
Reference: [1] Patent: CN108084115, 2018, A, . Location in patent: Paragraph 0086; 0090
  • 19
  • [ 106-94-5 ]
  • [ 106092-09-5 ]
  • [ 104632-26-0 ]
Reference: [1] Patent: WO2008/41240, 2008, A1, . Location in patent: Page/Page column 18
  • 20
  • [ 106092-09-5 ]
  • [ 104632-26-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 3, p. 494 - 498
[2] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1125 - 1129
[3] Patent: WO2011/21214, 2011, A2,
[4] Patent: CN107540633, 2018, A,
  • 21
  • [ 123-38-6 ]
  • [ 106092-09-5 ]
  • [ 104632-25-9 ]
Reference: [1] Patent: CN104496936, 2017, B, . Location in patent: Paragraph 0057; 0063; 0064; 0065; 0066
  • 22
  • [ 106092-09-5 ]
  • [ 104632-25-9 ]
Reference: [1] Patent: WO2011/21214, 2011, A2,
[2] Tetrahedron Asymmetry, 2014, vol. 25, # 16-17, p. 1239 - 1245
[3] Patent: WO2015/155704, 2015, A1,
[4] Patent: KR101546713, 2015, B1,
[5] Patent: CN104496936, 2017, B,
[6] Patent: CN107540633, 2018, A,
Same Skeleton Products
Historical Records