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[ CAS No. 1369761-01-2 ] {[proInfo.proName]}

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Chemical Structure| 1369761-01-2
Chemical Structure| 1369761-01-2
Structure of 1369761-01-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1369761-01-2 ]

CAS No. :1369761-01-2 MDL No. :MFCD28348366
Formula : C20H28ClN7O3S Boiling Point : -
Linear Structure Formula :- InChI Key :IYULGYKOHUAYCG-UHFFFAOYSA-N
M.W : 482.00 Pubchem ID :56960607
Synonyms :
PRT2070 hydrochloride;PRT062070 hydrochloride;Cerdulatinib hydrochloride

Calculated chemistry of [ 1369761-01-2 ]

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.45
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 133.47
TPSA : 141.93 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.73
Log Po/w (WLOGP) : 2.23
Log Po/w (MLOGP) : 0.72
Log Po/w (SILICOS-IT) : -0.28
Consensus Log Po/w : 1.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.3
Solubility : 0.0243 mg/ml ; 0.0000504 mol/l
Class : Moderately soluble
Log S (Ali) : -5.36
Solubility : 0.00208 mg/ml ; 0.00000432 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.84
Solubility : 0.00695 mg/ml ; 0.0000144 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.61

Safety of [ 1369761-01-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1369761-01-2 ]

* 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.

  • Downstream synthetic route of [ 1369761-01-2 ]

[ 1369761-01-2 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 611400-14-7 ]
  • [ 2306273-23-2 ]
  • [ 1369761-01-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-[4-(ethylsulfonyl)-1-piperazin-1-yl]phenylamine; C8H9ClN4O In 1-methyl-pyrrolidin-2-one at 80 - 90℃; Stage #2: With hydrogenchloride In ethanol; water; dimethyl sulfoxide at 75℃; for 12h; 2.2.2.3; 3 Step 2.3 Cerdulatinib was synthesized by addition of Compound B to the NMP solution containing Compound A-i obtained from Step 2.2 after water wash and solvent swap. In different batches, addition of Compound B was conducted under three different conditions: basic conditions, acidic conditions and neutral conditions.“Basic conditions” Under the basic conditions, 1.0 equivalent of DIPEA was added at the beginning of the reaction at temperatures between 105-110 °C, and a reaction time was 12-16 hrs. After isolation, which comprises precipitating cerdulatinib with water, filtration and washing, cerdulatinib was obtained in 69 % yield with a purity of about 90 %.“Acid conditions” Under the acid conditions, 1.2 equivalents of aqueous HCl was addition at the beginning of the reaction. The reaction proceeded at a temperature of about 80 °C for 6-7 hrs to provide cerdulatinib HCl salt. At the end of reaction, i .2 equivalents of DIPEA were added, and after isolation, cerdulatinib was obtained with a purity of 93.4 % and a yield of 78 %.“Neutral conditions” Under the neutral conditions, no acids or bases were added at the beginning of the reaction. The reaction proceeded at 80-90 °C during 8-i6 hrs. At the end of the reaction, 1.0 equivalent of DIPEA was added in order to neutralize the HC1 generated during the reaction. Cerdulatinib was isolated in a 90 % yield with a purity of 9 1-92 %. Alternatively, the reaction was run at 90 °C for 8-12 hrs followed by addition of 1.0 equivalent of TEA. Water was then added and the resulting cerdulatinib precipitation was filtered and washed a mixture of NIVIP and water, followed by water wash, providing cerdulatinib with purities between 94.7 % and 97.9 % in average yield of 87 %.Example 3. Preparation of Cerdulatinib HC1 Salt. Cerdulatinib was dissolved in DMSO at 75 °C followed by addition of ethanol and 2equivalents of HC1 (iN). The mixture was stirred at 75 ± 5 °C for 12 hrs and then cooled to 20± 5 °C. The resulting suspension was filtrated and the solid was washed by slurrying in ethanolthree times in the reactor, before being dried. Cerdulatinib HC1 salt was obtained with a purityof 99.19% and yield of 92%.
  • 2
  • [ 611400-14-7 ]
  • [ 1369761-02-3 ]
  • [ 1369761-01-2 ]
YieldReaction ConditionsOperation in experiment
35.44 kg Stage #1: C9H12N4OS With 3-chloro-benzenecarboperoxoic acid In 1-methyl-pyrrolidin-2-one at 0 - 25℃; for 1h; Large scale; Stage #2: 4-[4-(ethylsulfonyl)-1-piperazin-1-yl]phenylamine at 40℃; for 21.3h; Large scale; Stage #3: With hydrogenchloride In ethanol; water; dimethyl sulfoxide at 72.9 - 75℃; for 1h; Large scale; 1.2; 1.3; 4.4.3; 4.4.4 Step 2: Synthesis of Cerdulatinib 235 Kg of NMP, and 32.1 kg of Compound C PGE were charged to a reactor. The internal temperature was set at between 0-10 °C. 72.95 Kg of mCPBA were charged while keeping the temperature under 5 °C. The mixture was then warmed up to 25°C and stirred for 1 hr. IPC showed that residual content of Compound C was 0.00 % for oxidative reaction. The mixture was kept stirring at 25 °C for a further hour. To the above mixture, 40.05 kg of Compound B was added. The internal temperature was set at 40 °C and the mixture was stirred o.n. for 17 hrs and 17 minutes, and then for additional 4 hrs. IPC showed that residual content of Compound A-2 + Compound A-3 was 2.05 %. The mixture was cooled down to 3 °C, and a pre-cooled basic solution of water (642 L) and NaHCO3 (48 kg) was added to the mixture. The mixture was stirred for 1 hr and then water (193 L) was added keeping the internal temperature between 0-10 °C. The mixture was stirred for 40 minutes. Solid was isolated by filtration (filter-dryer equipped with 20 tm mesh) keeping squeezing the cake with both N2/vacuum for 51 hrs. Cerdulatinib PGU (106.9 kg) was then re-charged in the reactor and slurred at 25°C for9 hrs with water (1434 L). Solid was isolated by filtration (filter-dryer equipped with 20 tm mesh cloth) keeping squeezing the cake with both N2/vacuum for 60 hrs. Wet solid was respectively slurred and squeezing four times more in the filter-dryer using water (877 L). Solid was then forwarded to the filter-dryer for isolation and drying (43 °C undervacuum for 20 hrs). Cerdulatinib PGE overall yield was 88 % (63.76 kg) with purity of 90.84%. Step 3: Synthesis of Cerdulatinib HC1 Salt 252 Kg of DMSO and 56.2 kg of cerdulatinib were charged in the reactor. The mixture was warmed up to 75 °C and stirred till complete dissolution. 664 Kg of EtOH abs. was added and the reaction was stirred for 30 minutes. Keeping the internal temperature in between 70-80°C (72.9°C), an acidic solution made by mixing 347 kg of water and 43 kg of HC1 33% w/w was added. The reaction was stirred for further 30 minutes. The mixture was then cooled down to 20 °C and stirred for 19 hrs. Solid was then forwarded to the filter-dryer (20 tm mesh cloth) for isolation. Wet solid was respectively slurred and squeezing twice directly in the filter dryer using EtOH (1073 L), and then dried (at 35 °C under vacuum for 50 hrs). Cerdulatinib HC1 salt yield was 58.4 % (35.44 kg) with a purity of 99.41 %.
  • 3
  • [ 23945-44-0 ]
  • [ 1369761-01-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: phosphorus pentachloride / 80 - 105 °C 2.1: ammonia / 2-methyltetrahydrofuran / 1 h / Cooling 3.1: 2-methyltetrahydrofuran / Cooling 4.1: 1-methyl-pyrrolidin-2-one / 80 - 90 °C 4.2: 12 h / 75 °C
  • 4
  • [ 2972-52-3 ]
  • [ 1369761-01-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ammonia / 2-methyltetrahydrofuran / 1 h / Cooling 2.1: 2-methyltetrahydrofuran / Cooling 3.1: 1-methyl-pyrrolidin-2-one / 80 - 90 °C 3.2: 12 h / 75 °C
  • 5
  • [ 1240390-28-6 ]
  • 4-(cyclopropylamino)-2-({4-[4-(ethylsulfonyl)piperazin-1-yl]phenyl}amino)pyrimidine-5-carboxamide hydrochloride [ No CAS ]
  • 6
  • [ 5909-24-0 ]
  • [ 1369761-01-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 2 h / 15 - 42 °C / Inert atmosphere 2.1: formamide; sodium ethanolate / N,N-dimethyl-formamide / 1 h / 0 - 50 °C / Large scale 3.1: 3-chloro-benzenecarboperoxoic acid / 1-methyl-pyrrolidin-2-one / 1 h / 0 - 25 °C / Large scale 3.2: 21.3 h / 40 °C / Large scale 3.3: 1 h / 72.9 - 75 °C / Large scale
  • 7
  • [ 651734-65-5 ]
  • 4-(cyclopropylamino)-2-({4-[4-(ethylsulfonyl)piperazin-1-yl]phenyl}amino)pyrimidine-5-carboxamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: formamide; sodium ethanolate / N,N-dimethyl-formamide / 1 h / 0 - 50 °C / Large scale 2.1: 3-chloro-benzenecarboperoxoic acid / 1-methyl-pyrrolidin-2-one / 1 h / 0 - 25 °C / Large scale 2.2: 21.3 h / 40 °C / Large scale 2.3: 1 h / 72.9 - 75 °C / Large scale
Multi-step reaction with 3 steps 1.1: formamide; sodium ethanolate / N,N-dimethyl-formamide / 1 h / 0 - 50 °C / Large scale 2.1: 3-chloro-benzenecarboperoxoic acid / 1-methyl-pyrrolidin-2-one / 1 h / 0 - 25 °C / Large scale 2.2: 21.28 h / 40 °C / Large scale 3.1: hydrogenchloride / dimethyl sulfoxide; ethanol; water / 19.5 h / 20 - 80 °C / Large scale 3.2: 19.5 h / 20 - 80 °C / Large scale
  • 8
  • [ 1369761-02-3 ]
  • [ 1369761-01-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 3-chloro-benzenecarboperoxoic acid / 1-methyl-pyrrolidin-2-one / 1 h / 0 - 25 °C / Large scale 1.2: 21.28 h / 40 °C / Large scale 2.1: hydrogenchloride / dimethyl sulfoxide; ethanol; water / 19.5 h / 20 - 80 °C / Large scale 2.2: 19.5 h / 20 - 80 °C / Large scale
  • 9
  • [ 1198300-79-6 ]
  • 4-(cyclopropylamino)-2-({4-[4-(ethylsulfonyl)piperazin-1-yl]phenyl}amino)pyrimidine-5-carboxamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
35.44 kg 252 Kg of DMSO and 56.2 kg of Compound I were charged in the reactor. The mixture was warmed up to 75 C and stirred till complete dissolution. 664 Kg of EtOH abs. was added and the reaction was stirred for 30 minutes. Keeping the internal temperature in between 70-80C (72.9C), an acidic solution made by mixing 347 kg of water and 43 kg of HC1 33% w/w was added. The reaction was stirred for further 30 minutes. The mixture was then cooled down to 20 C and stirred for 19 hours. Solid was then forwarded to the filter- dryer (20 pm mesh cloth) for isolation. Wet solid was respectively slurried and squeezing twice directly in the filter-dryer using EtOH (1073 L), and then dried (at 35 C under vacuum for 50 hours). Compound I hydrochloride salt yield was 58.4 % (35.44 kg) with a purity of 99.41 %.
  • 10
  • [ 1198300-79-6 ]
  • C20H27N7O3S*1.5ClH [ No CAS ]
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