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Chemical Structure| 172015-79-1
Chemical Structure| 172015-79-1
Structure of 172015-79-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 172015-79-1 ]

CAS No. :172015-79-1 MDL No. :MFCD12546177
Formula : C11H13Cl2N5O Boiling Point : -
Linear Structure Formula :- InChI Key :VZJFPECAPXUELG-HHQFNNIRSA-N
M.W : 302.16 Pubchem ID :23654840
Synonyms :

Calculated chemistry of [ 172015-79-1 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.36
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 75.57
TPSA : 89.85 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.52
Log Po/w (WLOGP) : 1.98
Log Po/w (MLOGP) : 0.67
Log Po/w (SILICOS-IT) : 0.23
Consensus Log Po/w : 0.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.89
Solubility : 0.39 mg/ml ; 0.00129 mol/l
Class : Soluble
Log S (Ali) : -3.02
Solubility : 0.292 mg/ml ; 0.000965 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.89
Solubility : 3.9 mg/ml ; 0.0129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.45

Safety of [ 172015-79-1 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P260-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P314-P333+P313-P501 UN#:N/A
Hazard Statements:H302-H317-H318-H372-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 172015-79-1 ]

* 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 [ 172015-79-1 ]
  • Downstream synthetic route of [ 172015-79-1 ]

[ 172015-79-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 171887-04-0 ]
  • [ 172015-79-1 ]
YieldReaction ConditionsOperation in experiment
76% With hydrogenchloride; orthoformic acid triethyl ester In water at 0 - 10℃; for 1 h; N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide (0.1762 mol) was added to trietylorthoformate (7V). Cooled the mass to 0-5° C., hydrochloride acid (0.7V) was added at 0-10° C. After addition maintained the mass for 60 min at 0-5° C. Allowed the mass to room temperature and maintained for 16-18 hrs at. Filtered the mass and purified in methanol. (Yield: 76percent, HPLC purity: 98.69percent).
72.2% With hydrogenchloride; orthoformic acid triethyl ester In ethanol at 0 - 10℃; for 10 h; Compound I (53.2 g, 0.36 mol) was added to absolute ethanol (700 mL) under nitrogen and then added Sodium bicarbonate (100 g, 0.94 mol) was stirred at room temperature for 0.5 hour; Compound II (74.5 g, 0.36 mol) was added to the above reaction system, and the temperature was raised to 75-80 ° C, and the reaction was allowed to cool for 3 hours and then cooled to room temperature. Perform suction filtration. To the filtrate was added triethyl orthoformate (251.5 g, 1.69 mol), and the mixture was stirred at 0 to 10 °C.An ethanolic hydrochloric acid solution (6.0 mol/L, 150 mL) was added dropwise to the reaction system during the stirring.After the addition is completed,Insulation reaction for 10 hours,Then suction filtration, drying,100 g of brownish yellow abacavir intermediate was obtained.Wherein the molar yield of the obtained abacavir intermediate is 92.0percent;HPLC purityThe ratio was 93.90percent, the absorbance (λ = 420 nm) = 0.36, and the absorbance (λ = 450 nm) = 0.31.
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2000, vol. 19, # 1-2, p. 297 - 327
[2] Patent: US2017/233329, 2017, A1, . Location in patent: Paragraph 0054; 0055
[3] Patent: CN107641122, 2018, A, . Location in patent: Paragraph 0016; 0049; 0055-0056; 0059-0073; 0076
  • 2
  • [ 122-51-0 ]
  • [ 171887-04-0 ]
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YieldReaction ConditionsOperation in experiment
82% With hydrogenchloride In tetrahydrofuran; industrial methylated spirit; water at 0 - 25℃; Example A [00029] Preparation of (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt. [00030] A suspension of (1R,4S)-cis-[4-(hydroxymethyl)-2-cyclopentene-1-yl]carbamic acid, 1, 1-dimethylethyl ester (100 g) in industrial methylated spirit (IMS) (600 ml) was treated with concentrated hydrochloric acid (48 ml, 1.2 molar equivalents) and the resultant solution was heated to the boil over about 0.5 h. Heating under reflux was maintained for about 2.5 h. The solution was cooled to 20 to 25° C. and diluted with IMS (600 ml). Triethylamine (170 ml) was added followed by N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide (WO95/21161) (97 g). The suspension was heated under reflux for about 17 h to give a clear solution, which was cooled to 25 to 30° C. and finely divided potassium carbonate (169 g) was added. The suspension was stirred in this temperature range for about 0.5 h then cooled to 0 to 5° C. and the solids filtered off. The solids were washed with IMS (3.x.180 ml and 1.x.140 ml) and the combined filtrates and washings were concentrated under reduced pressure to a red gum. This was redissolved in IMS (1000 ml) and the solution was concentrated under reduced pressure to a gum. The dilution and re-concentration were repeated twice more, and the final gum was redissolved in IMS (350 ml). [00031] Meanwhile, a mixture of triethylorthoformate (900 ml) and tetrahydrofuran (THF) (400 ml) was prepared and cooled to 0 to 5° C. Concentrated hydrochloric acid (80 ml) was added, maintaininglthe temperature between 0 and 10° C., and more THF (100 ml,) was then added. To this mixture was added the IMS concentrate prepared above, which was rinsed in with IMS (100 ml). The mixture was warmed to 20 to 25° C. and seeded with authentic (1S,4R)-c-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt and stirring continued for about 20 h. The slurry was filtered, the solid was washed with a mixture of tert-butyl methyl ether and IMS (9/1, 3.x.300 ml) and dried in vacuo at 40 to 45° C. to give the title compound (117 g, 82percent) as a fawn coloured solid 1H-NMR (DMSO-d6)δ: 8.38(s, 1, purine CH), 7.50(br m, ca 5, NH3+, OH, HOD), 6.20(m, 1, CH) 5.94(m, 1, CH), 5.49(m, 1, NCH), 3.46(m, 2, OCH2), 2.91(br m, 1, CH), 2.70-2.60(m, 1, CH), 1.75-1.66(m, 1, CH).
81% With hydrogenchloride In industrial methylated spirit; water at 0 - 25℃; Example B Preparation of (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-l-methanol hydrochloride salt. [00033] A suspension of (1R,4S)-cis-[4-(hydroxymethyl)-2-cyclopentene-1-yl]carbamic acid, 1, 1-dimethylethyl ester (100 g) in industrial methylated spirit (IMS) (600 ml) was treated with concentrated hydrochloric acid (48 ml, 1.2 molar equivalents) and the resultant solution was heated to the boil over about 0.5 h. Heating under reflux was maintained for about 3 h. The solution was cooled to 20 to 25° C. and sodium bicarbonate (103.4 g) was added followed by N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide (WO95/21161) (97g) and IMS (600 ml). The suspension was heated under reflux for about 4 h and then cooled to about -5° C. After stirring at this temperature for about 1h, the solids were filtered off and washed with IMS (2.x.100 ml). The combined filtrates and washings were concentrated under reduced pressure to a residual volume of about 400 ml. This was redissolved in IMS (1000 ml) and the solution was concentrated under reduced pressure to a gum. The dilution and re-concentration were repeated twice more, and the final gum was redissolved in IMS (350 ml). [00034] Meanwhile, triethylorthoformate (900 ml) was cooled to 0 to 5° C. and concentrated hydrochloric acid (80 ml) was added, maintaining the temperature between 0 and 10° C. To this mixture was added the IMS concentrate prepared above, which was rinsed in with IMS (600 ml). The mixture was warmed to 20 to 25° C. and seeded with authentic (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt and stirring was continued for about 7 h. The slurry was filtered, and the solid was washed with IMS (2.x.150 ml) and dried in vacuo at 40 to 45° C. to give the title compound (114 g, 81percent) as a fawn coloured solid, spectroscopically identical to the product of Example A.; Example C [00035] Preparation of (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt.A suspension of (1R,4S)-cis-[4-(hydroxymethyl)-2-cyclopentene-1-yl]carbamic acid, 1, 1-dimethylethyl ester (100 g) in industrial methylated spirit (IMS) (600 ml) was treated with concentrated hydrochloric acid (48 ml, 1.2 molar equivalents) and the resultant solution was heated to the boil over about 0.5 h. Heating under reflux was maintained for about 3 h. The solution was cooled to 20 to 25° C. and sodium bicarbonate (103.4 g) was added followed by N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide (WO95/21161) (97g) and IMS (600 ml). The suspension was heated under reflux for about 4 h and then cooled to about -5° C. After stirring at this temperature for about 1h, the solids were filtered off and washed with IMS (2.x.100 ml). The combined filtrates and washings were concentrated under reduced pressure to a residual volume of about 400 ml. This was redissolved in IMS (1000 ml) and the solution was concentrated under reduced pressure to a gum. The dilution and re-concentration were repeated twice more, and the final gum was redissolved in IMS (350 ml). [00034] Meanwhile, triethylorthoformate (900 ml) was cooled to 0 to 5° C. and concentrated hydrochloric acid (80 ml) was added, maintaining the temperature between 0 and 10° C. To this mixture was added the IMS concentrate prepared above, which was rinsed in with IMS (600 ml). The mixture was warmed to 20 to 25° C. and seeded with authentic (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt and stirring was continued for about 7 h. The slurry was filtered, and the solid was washed with IMS (2.x.150 ml) and dried in vacuo at 40 to 45° C. to give the title compound (114 g, 81percent) as a fawn coloured solid, spectroscopically identical to the product of Example A.Example C [00035] Preparation of (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt. [00036] A suspension of (1R,i4S)-cis-[4-(hydroxymethyl)-2-cyclopentene-1-yl]carbamic acid, 1, 1-dimethylethyl ester (72.5 kg) in industrial methylated spirit (IMS) (435 L) and water (about 200 L) was treated with concentrated hydrochloric acid (36.5 L, 1.2 molar equivalents) and the resultant solution was heated to the boil over about 1.5 h. Heating under reflux was maintained for about 2 h. The solution was cooled to 20 to 25° C. and sodium bicarbonate (75 kg) was added followed by N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide (WO95/21161) (70 kg) and IMS (435 L). The suspension was heated under reflux for about 4 h and then cooled to about -5° C. After stirring at this temperature for about 1 h, the solids were filtered off and washed with IMS (2.x.144 L). The combined filtrates and washings were concentrated under reduced pressure to a residual volume of about 290 L. This was diluted with IMS (about 300 L) and the solution was concentrated under reduced pressure to a residual volume of about 290 L. The dilution and re-concentration were repeated twice more, and the final concentrate was diluted with IMS (610 L) and heated to about 35-40° C. The resultant mixture was filtered and the solids were washed with IMS (2.x.144 L) The combined filtrate's and washings were concentrated under reduced pressure to a residual volume of about 290 L and then diluted with IMS (217 L). [00037] Meanwhile, a mixture of triethylorthoformate (660 L), concentrated hydrochloric acid (58 L) and IMS (72 L) was prepared at 0 to 8° C., To this mixture was added the IMS concentrate prepared above, which was rinsed in with IMS (2.x.72 L). The mixture was warmed to 20 to 25° C. and seeded with authentic (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt and stirring was continued for about 7 h. The slurry was cooled to 18-21° C., filtered, and the solid was washed with IMS (72 L and 217 L) and dried in vacuo at 40 to 45° C. to give the title compound (81.7 kg, 79.5percent) as a fawn coloured solid, spectroscopically identical to the product of Example A. Example D [00038] Preparation of (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt. [00039] A suspension of (1R,14S)-cis-[4-(hydroxymethyl)-2-cyclopentene-1-yl]carbamic acid, 1, 1-dimethylethyl ester (10 g) in industrial methylated spirit (IMS) (60 ml) was treated with concentrated hydrochloric acid (5 ml, 1.2 molar equivalents) and the resultant solution was heated to the boil over about 0.5 h. Heating under reflux was maintained for about 3 h. The solution was cooled to 20 to 25° C. and weighed (45.7 g). A portion (14 g) was diluted with IMS (14 ml) and sodium bicarbonate (3.1 g) was added followed by 2,5-diamino-4,6-dichloropyrimidine (WO95/21161) (2.0 g). The suspension was heated under reflux for about 7 h and then cooled to about -5° C. The solids were filtered off and the combined filtrates and washings were concentrated under reduced pressure to a gum, which was redissolved in IMS (17 ml). [00040] Meanwhile, triethylorthoformate (21.4 ml) was cooled to 0 to 5° C. and concentrated hydrochloric acid (1.9 ml) was added, maintaining the temperature between 0 and 10° C. To this mixture was added the IMS solution prepared above, which was rinsed in with IMS (2.x.2.5 ml). The mixture was warmed to 20 to 25° C. and seeded with authentic (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt and stirring was continued for about 19 h. The slurry was filtered, and the solid was washed with IMS (2.x.4.5 ml) and dried in vacuo at 40 to 45° C. to give the title compound (2.06 g, 61percent) as a pale yellow solid, spectroscopically identical to the product of Example A.
Reference: [1] Patent: US6646125, 2003, B1, . Location in patent: Page/Page column 5
[2] Patent: US6646125, 2003, B1, . Location in patent: Page/Page column 5-6
  • 3
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Reference: [1] Patent: EP1857458, 2007, A1, . Location in patent: Page/Page column 5
  • 4
  • [ 171887-03-9 ]
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Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2000, vol. 19, # 1-2, p. 297 - 327
[2] Patent: CN107641122, 2018, A,
  • 5
  • [ 79200-56-9 ]
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Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2000, vol. 19, # 1-2, p. 297 - 327
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  • [ 136522-35-5 ]
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Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2000, vol. 19, # 1-2, p. 297 - 327
  • 7
  • [ 171887-02-8 ]
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Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2000, vol. 19, # 1-2, p. 297 - 327
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