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[ CAS No. 107-36-8 ] {[proInfo.proName]}

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Chemical Structure| 107-36-8
Chemical Structure| 107-36-8
Structure of 107-36-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 107-36-8 ]

CAS No. :107-36-8 MDL No. :MFCD00242599
Formula : C2H6O4S Boiling Point : -
Linear Structure Formula :- InChI Key :SUMDYPCJJOFFON-UHFFFAOYSA-N
M.W : 126.13 Pubchem ID :7866
Synonyms :
2-Hydroxyethanesulfonic acid

Calculated chemistry of [ 107-36-8 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 23.43
TPSA : 82.98 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) : -8.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : -1.17
Log Po/w (XLOGP3) : -1.57
Log Po/w (WLOGP) : -0.05
Log Po/w (MLOGP) : -1.51
Log Po/w (SILICOS-IT) : -0.94
Consensus Log Po/w : -1.05

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : 0.5
Solubility : 398.0 mg/ml ; 3.16 mol/l
Class : Highly soluble
Log S (Ali) : 0.34
Solubility : 273.0 mg/ml ; 2.16 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.58
Solubility : 476.0 mg/ml ; 3.78 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.28

Safety of [ 107-36-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P310+P330+P331-P303+P361+P353+P310-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501 UN#:3265
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 107-36-8 ]

* 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 [ 107-36-8 ]

[ 107-36-8 ] Synthesis Path-Downstream   1~85

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  • [ 328-39-2 ]
  • <i>N</i>-(2-hydroxy-ethanesulfonyl)-<i>dl</i>-leucine [ No CAS ]
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  • [ 143-28-2 ]
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  • [ 120256-31-7 ]
Reference: [1]Patent: FR715585,
  • 10
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  • [ 3370-35-2 ]
  • 2-(stearoylamino-methoxy)-ethanesulfonic acid [ No CAS ]
  • 11
  • [ 107-36-8 ]
  • [1,5,2,6]dioxadithiocane-2,2,6,6-tetraoxide [ No CAS ]
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  • [ 107-36-8 ]
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  • [ 107-36-8 ]
  • <i>N</i>-(2-hydroxy-ethanesulfonyl)-glycine [ No CAS ]
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  • [ 88916-83-0 ]
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  • [ 503-41-3 ]
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  • [ 461-42-7 ]
  • [ 107-36-8 ]
YieldReaction ConditionsOperation in experiment
With water; for 3h;Reflux; Ethionic acid, 206 g, is diluted with 800 mE of deionizedwater and heated to reflux for three hours to complete thehydrolysis to an aqueous solution containing isethionic acidand sulfuric acid, to which 80 g of sodium sulfate is added.About 120 g of calcium hydroxide is added slowly to bringthe pH to 8-9 and a white slurry of calcium sulfate is formed.Afier filtration and washing with deionized water, an aqueoussolution of sodium isethionate is obtained.
  • 19
  • [ 107-36-8 ]
  • [ 108-24-7 ]
  • 2-acetoxy-ethanesulfonic acid [ No CAS ]
  • 20
  • [ 107-36-8 ]
  • [ 99-05-8 ]
  • 3-(2-hydroxy-ethanesulfonylamino)-benzoic acid [ No CAS ]
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  • [ 118-92-3 ]
  • <i>N</i>-(2-hydroxy-ethanesulfonyl)-anthranilic acid [ No CAS ]
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  • [ 107-04-0 ]
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  • [ 106-93-4 ]
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  • [ 302-72-7 ]
  • <i>N</i>-(2-hydroxy-ethanesulfonyl)-DL-alanine [ No CAS ]
  • 25
  • [ 107-36-8 ]
  • [ 94-09-7 ]
  • 4-(2-hydroxy-ethanesulfonylamino)-benzoic acid [ No CAS ]
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  • [ 107-07-3 ]
  • [ 107-36-8 ]
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  • [ 71-36-3 ]
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  • 32
  • [ 6608-47-5 ]
  • [ 1184-84-5 ]
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  • 33
  • [ 107-36-8 ]
  • hexadecyl <2>betylate fluorosulfate [ No CAS ]
  • [ 80314-01-8 ]
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  • [ 7732-18-5 ]
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  • [ 107-07-3 ]
  • potassium disulfite [ No CAS ]
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  • 46
  • [ 64-67-5 ]
  • fume.H2SO4 [ No CAS ]
  • [ 64-17-5 ]
  • [ 107-36-8 ]
  • [ 7664-93-9 ]
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  • [ 7647-01-0 ]
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  • [ 107-68-6 ]
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  • [ 1184-84-5 ]
  • alkali [ No CAS ]
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  • 1-bromo-2-hydroxy-ethanesulfonic acid [ No CAS ]
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  • sodium amalgam [ No CAS ]
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  • [ 107-36-8 ]
  • chromic acid [ No CAS ]
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  • 1 mol SO3 [ No CAS ]
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  • [ 107-36-8 ]
  • [ 7664-93-9 ]
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  • [ 107-36-8 ]
  • H2S2O7 [ No CAS ]
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  • [ 74-85-1 ]
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  • [ 7446-11-9 ]
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  • [ 461-42-7 ]
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  • [ 7465-57-8 ]
  • aq. barium hydroxide solution [ No CAS ]
  • [ 107-36-8 ]
  • [ 75-50-3 ]
  • 64
  • irciniasulfonic acid O-methyl (Z)-15-docosenoate [ No CAS ]
  • [ 107-36-8 ]
  • deacyl irciniasulfonic acid [ No CAS ]
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  • irciniasulfonic acid O-methyl (5Z,9Z)-5,9-tetracosenoate [ No CAS ]
  • [ 107-36-8 ]
  • deacyl irciniasulfonic acid [ No CAS ]
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  • irciniasulfonic acid O-methyl tricosanoate [ No CAS ]
  • [ 107-36-8 ]
  • deacyl irciniasulfonic acid [ No CAS ]
  • 67
  • [ 107-36-8 ]
  • [ 855123-23-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; nitric acid; In water; at 5 - 60℃; for 0.25h;Product distribution / selectivity; EXAMPLE 1; The reader is cautioned that this procedure produces a material which is a powerful coronary vasodilator, which if uncontrollably admitted into the human body may cause increased heart rate, dizziness, headache, hallucinations, and even death. Since the properties of the compounds provided herein have not been fully investigated, it must be assumed a priori that they possess unknown effects on the human body and organs. In addition, nitric esters may spontaneously decompose, sometimes unprovoked, with explosive violence. Due care known only to those particularly skilled in the art of nitration must therefore be exercised when working with materials of this invention, to avoid catastrophe. At room temperature, thirty milliliters of concentrated nitric acid containing 70% by weight of HNO3 is poured into a 250 ml beaker, and to this nitric acid is slowly added sixty milliliters of concentrated sulfuric acid containing 98% by weight of H2SO4, with stirring. The temperature of the contents of the beaker rise to about 60 degrees centigrade, after which time the beaker containing the mixed acid is placed into an ice bath, until the temperature of the mixed acid has cooled to about 5 degrees centigrade. Subsequently, five milliliters of isethionic acid of about 98% purity is added dropwise to the mixed acid, with stirring, at such a rate that the temperature of the mixed acid is not permitted to rise above about 10 degrees centigrade. The contents of the beaker are permitted to rest for 15 minutes while being kept below about 10 degrees centigrade, after which time the contents of the beaker are poured slowly over about 300 grams of cracked ice contained in a 500 ml beaker. When the mixed acids contact the cracked ice, heat is generated, which melts a substantial portion of the ice. The remaining ice is allowed to melt, providing a total liquid volume of about 400 milliliters within the 500 ml beaker. At this stage, the liquid contains sulfuric acid, nitric acid, and the crude isethionyl nitrate product, which is an acid that corresponds to the formula in which M+, R1, and R2 are each hydrogen, and n=1, thus affording the compound having formula C2H5SNO6 having a formula weight of about 171.14. The aqueous solution containing the mixed acids was transferred to a 1000 ml separatory funnel and extracted with 3 thirty milliliter aliquots of ethyl ether, which yielded a pale yellow solution. The ether extracts were combined, dried (MgSO4), and evaporated to yield a slightly brown oily residue containing a high purity material which when diluted in approximately 100 times its volume of 190 proof grain alcohol was acidic to the taste, and which promptly caused the same symptoms as a small amount of glyceryl trinitrate (?NG?) when placed under my tongue. However, the effect of this novel substance seemed to be longer-lived than in my experiences with glyceryl trinitrate, which is surprising, since each molecule of the present substances contain only one nitric ester unit per molecule, compared with the three nitric ester units in the NG molecule. I therefore surmise that the remainder of the molecule of the instant substances somehow hinder their metabolism by the human organism, and are therefore able to exert a longer-lasting effect, which in my experience was on the order of about 1 hour. In the case of NG, a similar effect is only observed for about 7-8 minutes in me personally, and possibly up to a maximum of about 15 minutes. Therefore, the compounds of this invention are anticipated to be of great therapeutic value, owing not only to their apparent increased potency over NG, but also owing to their improved stability as described below.
With nitric acid; phosphorus pentoxide; In water; at 0 - 10℃;Product distribution / selectivity; An alternate method for preparing IN is to add 50 milliliters of strong (70%) nitric acid to a 100 ml beaker housed in an ice bath, and to add 10 grams of phosphoric oxide P2O5) to the nitric acid slowly in about 1 gram quantities, allowing for cooling and with stirring. The contents of the beaker are then chilled to 5 degrees centigrade and 7 ml of isethionic acid are added slowly with stirring while maintaining the beaker contents below about 10 degrees centigrade. Extraction with ether and worked up as described earlier affords IN.
  • 68
  • [ 571190-30-2 ]
  • [ 107-36-8 ]
  • PD 0332991 isethionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.8% In methanol; at -8 - 20℃;Conversion of starting material; EXAMPLE 7 Preparation of A MONO-ISETHIONATE salt of 6-ACETYL-8-CVCLOPENTYL-5-METHYL-5- IPERAZIN-1-VL-PVRIDIN-2-VLAMINO)-8H-PVRIDOF2,. 3-DLPVRIMIDIN-7-ONE (Form B) The free base (Formula 1, 0. 895 mg, 2 MMOL) was mixed with 10 mL of MeOH and seeded with 33 mg of A MONO-ISETHIONATE SALT OF THE COMPOUND OF FORMULA L (FORM B). THEN 5.6 mL of A 0. 375 M solution of isethionic acid in MeOH (2. 1 MMOL) was added in 10 even portions over 75 min time period. The mixture was stirred for an additional hour and a sample was TAKEN FOR PXRD ANALYSIS. IT CONFIRMED FORMATION OF CRYSTALLINE FORM B. THE MIXTURE WAS stirred at RT overnight and another PXRD was taken. There was no change in the crystal form. The mixture was cooled in a refrigerator AT-8C overnight, filtered, and dried at 50C in a vacuum oven to give 1.053 g (91.8 % of theory) of the above-named compound (Form B). HPLC-99.8 %, CHNS, H-NMR, IR are consistent with the structure, PXRD-Form B.
52.5% In methanol; at 20℃; for 3h; 5L three bottles, put into 290.0g (0.65mol) free base, 1.2L methanol, stirred at room temperature, the moment after dropping 98.2g isethionic (0.78mol) and 500mL methanol mixture, the suspension system gradually became clear there are large amount of solid precipitated, continued stirring for 3 hours at room temperature, suction filtered, the filter cake rinsed with methanol, 45 blast drying to give a pale yellow solid, constant weight 196.0g, a yield of 52.5%.
In methanol; water;pH 5.2; EXAMPLE 4 Preparation of A mono-isethionate salt of 6-ACETVL-8-CVCLOPENTYL-5-METHYL-2- (5- PIPERAZIN-1-YL-PYRIDIN-2-VLAMINO)-8H-PVRIDOF2. 3-DLPVRIMIDIN-7-ONE (Form B) To A slurry of 6-ACETYL-8-CYCLOPENTYL-5-METHYL-2- (5-PIPERAZIN-1-YL-PYRIDIN-2-YLAMINO)- 8H-PYRIDO [2, 3-DIPYRIMIDIN-7-ONE (7.0 g, 15.64 MMOL, prepared as in Example 3 following contact with NaOH) dispersed in 250 mL of water was added drop-wise 30 mL OF A 0. 52 M solution of isethionic acid in MeOH (15. 64 MMOL) to A pH of 5. 2. The solution was filtered through A glass filter (fine) and the clear solution was freeze-dried to give 9. 4 G of the amorphous salt. The amorphous salt (3. 16 g) was mixed with 25 mL of MEC) H AND AFTER almost complete dissolution A new precipitate formed. Another 25 mL of MeOH was added and the mixture was stirred at 46C to 49C for four hours. The mixture was slowly cooled to 32C and put in a cold room (+4C) overnight. A sample was taken for PXRD, which indicated formation of Form B. The mixture was filtered and the precipitate was dried overnight at 50C in a vacuum oven. This furnished 2.92 G of the mono-isethionate salt of the compound of Formula 1 in 92 % yield.
In methanol; water;pH 5.2; Preparation 4 Preparation of a mono-isethionate salt of 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (Form B) To a slurry of 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (7.0 g, 15.64 mmol, prepared as in Example 3 following contact with NaOH) dispersed in 250 mL of water was added drop-wise 30 mL of a 0.52 M solution of isethionic acid in MeOH (15.64 mmol) to a pH of 5.2. The solution was filtered through a glass filter (fine) and the clear solution was freeze-dried to give 9.4 g of the amorphous salt. The amorphous salt (3.16 g) was mixed with 25 mL of MeOH and after almost complete dissolution a new precipitate formed. Another 25 mL of MeOH was added and the mixture was stirred at 46 C. to 49 C. for four hours. The mixture was slowly cooled to 32 C. and put in a cold room (+4 C.) overnight. A sample was taken for PXRD, which indicated formation of Form B. The mixture was filtered and the precipitate was dried overnight at 50 C. in a vacuum oven. This furnished 2.92 g of the mono-isethionate salt of the compound of Formula 1 in 92% yield. HPLC-99.25%, PXRD-Form B, CHNS, H-NMR were consistent with the structure.

  • 69
  • tert‑butyl 4‑(6‑((6‑(1‑butoxyvinyl)‑8‑cyclopentyl‑5‑methyl‑7‑oxo‑7,8‑dihydropyrido[2,3‑d]pyrimidin‑2‑yl)amino)pyridin‑3‑yl)piperazine‑1‑carboxylate [ No CAS ]
  • [ 107-36-8 ]
  • PD 0332991 isethionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% EXAMPLE 12 Preparation of a mono-isethionate salt of 6-ACETVL-8-CYCLOPENTYL-5-METHYL-2- 5- PIPERAZIN-1-VL-VRIDIN-2-YLAMINO)-8H-PVRIDO [2, 3-DLPVRIMIDIN-7-ONE (FORM B) A 22-L, three-necked, round-bottomed flask, equipped with a mechanical stirrer, A thermocouple, and A nitrogen inlet/outlet vented through A silicone oil bubbler was placed under a nitrogen atmosphere and charged with 4-{6-[6-(1-butoxy-vinyl)-8-cyclopentyl-5- methyl-7-oxo-7, 8-DIHYDRO-PYRIDO [2, 3-DJPYRIMIDIN-2-YLAMINO]-PYRIDIN-3-YL}-PIPERAZINE-1- carboxylic acid TERT-BUTYL ester (725 g, 1.20 mol, prepared as in Example 11) and MEOH (14 L). The slurry was stirred at RT as it was charged with a solution of isethionic acid (530 g, 4.20 mol, prepared as in Example 10), MEOH (1.5 L), and water (70 mL, 3.89 MOL). The resulting slurry was heated to 55C over 30 minutes and then stirred at 55C for 30 minutes. A solution of 175 g (1.73 mol) of Et3N (ALDRICH) in 200 mL of MeOH was charged to the slurry as it was cooled to 30C. The slurry was held at 30C as a solution of 128 g (1.26 mol) of Et3N in 2 L of MEOH was added dropwise over 6 hours. The resulting slurry was sampled to determine crystal form (Form B). The slurry was cooled and held at 5C for 15 minutes and was subsequently filtered through a coarse-fritted filter. The resulting filter cake was washed with multiple washes of 200 mL of COLD MEOH. The solid product was dried at 55T under vacuum to yield 710 g (91 % yield) of the title compound as yellow crystals.
91% Preparation 12 Preparation of a mono-isethionate salt of 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (Form B) A 22-L, three-necked, round-bottomed flask, equipped with a mechanical stirrer, a thermocouple, and a nitrogen inlet/outlet vented through a silicone oil bubbler was placed under a nitrogen atmosphere and charged with 4-{6-[6-(1-butoxy-vinyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester (725 g, 1.20 mol, prepared as in Example 11) and MeOH (14 L). The slurry was stirred at RT as it was charged with a solution of isethionic acid (530 g, 4.20 mol, prepared as in Example 10), MeOH (1.5 L), and water (70 mL, 3.89 mol). The resulting slurry was heated to 55 C. over 30 minutes and then stirred at 55 C. for 30 minutes. A solution of 175 g (1.73 mol) of Et3N (ALDRICH) in 200 mL of MeOH was charged to the slurry as it was cooled to 30 C. The slurry was held at 30 C. as a solution of 128 g (1.26 mol) of Et3N in 2 L of MeOH was added dropwise over 6 hours. The resulting slurry was sampled to determine crystal form (Form B). The slurry was cooled and held at 5 C. for 15 minutes and was subsequently filtered through a coarse-fritted filter. The resulting filter cake was washed with multiple washes of 200 mL of cold MeOH. The solid product was dried at 55 C. under vacuum to yield 710 g (91% yield) of the title compound as yellow crystals. It is to be understood that the above description is intended to be illustrative and not restrictive. Many embodiments will be apparent to those of skill in the art upon reading the above description. The scope of the invention should, therefore, be determined not with reference to the above description, but should instead be determined with reference to the appended claims, along with the full scope of equivalents to which such claims are entitled. The disclosures of all articles and references, including patents, patent applications, and patent publications, are incorporated herein by reference in their entirety and for all purposes.
With methanol; water; at 55 - 60℃; for 6h; Example 6: Preparation of e-acetyl-delta-cyclopentyl-S-methyl^^S-piperazin-i-yl-pyridin^-ylaminoJ-delta/-/- pyrido[2,3-c(]pyrimidin-7-one11.6 g (1.00 eq, 19.2mmol) of-intermediate 5, water- (10.1 equiv; 193 mmoles; 3.48 ml 3.48 g) and methanol (3.62 moles; 146 ml 116 g) were combined and heated to 55-600C. lsethionic acid was added slowly until a clear solution was obtained; 3.3g isethionic acid solution was necessary to reach this end point. The resulting clear orange solution was filtered through paper and rinsed through with 20ml methanol, after which the filtrate was reheated to 55-600C and the remaining isethionic acid was added (a total of 9.93g was added). The reaction mixture precipitated and thickened for 6 hours.after which it was cooled and held at 30-350C while triethylamine ( 2.92g; 28.8mmoles) was added slowly as a 10% solution in methanol over 12hrs. About halfway through the addition of triethylamine, desired polymorphic seeds were added to help formation of the desired polymorph. The resulting slurry was cooled and held at 5C for 15 minutes and the crystals were filtered and washed with methanol. The solid product was dried in vacuo at 550C to obtain 11 g of yellow crystals of the title compound.
  • 70
  • [ 1562-00-1 ]
  • [ 107-36-8 ]
YieldReaction ConditionsOperation in experiment
91.1% With hydrogenchloride; In isopropyl alcohol; at 20 - 50℃; EXAMPLE 10 Preparation of isethionic acid (2-HYDROXY-ETHANESULFONIC acid) A 5-L, four-necked, round-bottomed flask, equipped with mechanical stirrer, thermocouple, gas sparger, and an atmosphere vent through a water trap was charged with 748 g (5. 05 mol) of sodium isethionate (ALDRICH), and 4 L of IPA. The SLURRY was stirred at RT. An ice bath was used to keep the internal temperature below 50C as 925 g (25. 4 mol) of hydrogen chloride gas (ALDRICH) was sparged into the system at a rate such that it dissolved as fast as it was added (as noted by lack of bubbling through the water trap). Sufficient HCI gas was added until the system was saturated (as noted by the start of bubbling through the water trap). During the addition of HCI, the temperature rose to 45C. The slurry was cooled to RT and filtered over a COARSE-FRITTED filter. The cake was washed with 100 mL of IPA and the. cloudy filtrate was filtered through a 10-20mu filter. The resulting clear, colorless filtrate was concentrated under reduced pressure on a rotary evaporator, while keeping the bath temperature below 50C. The resulting 1.07 kg of clear, light yellow oil was diluted with 50 mL of tap water and 400 mL of toluene and concentrated under reduced pressure on a rotary evaporator for three days, while keeping the bath temperature below 50C. The resulting 800 g of clear, light yellow oil was diluted with 500 mL of toluene and 250 mL of IPA and concentrated under reduced pressure on a rotary evaporator for 11 days, keeping the bath temperature below 50C. The resulting 713 g of clear, light yellow oil was titrated at 81 wt % (580 g, 91. 1% yield) containing 7.9 wt % water and 7.5 wt % IPA.
91.1% With hydrogenchloride; In isopropyl alcohol; at 20 - 50℃; Preparation 10 Preparation of isethionic acid (2-hydroxy-ethanesulfonic acid) A 5-L, four-necked, round-bottomed flask, equipped with mechanical stirrer, thermocouple, gas sparger, and an atmosphere vent through a water trap was charged with 748 g (5.05 mol) of sodium isethionate (ALDRICH), and 4 L of IPA. The slurry was stirred at RT. An ice bath was used to keep the internal temperature below 50 C. as 925 g (25.4 mol) of hydrogen chloride gas (ALDRICH) was sparged into the system at a rate such that it dissolved as fast as it was added (as noted by lack of bubbling through the water trap). Sufficient HCl gas was added until the system was saturated (as noted by the start of bubbling through the water trap). During the addition of HCl, the temperature rose to 45 C. The slurry was cooled to RT and filtered over a coarse-fritted filter. The cake was washed with 100 mL of IPA and the cloudy filtrate was filtered through a 10-20mu filter. The resulting clear, colorless filtrate was concentrated under reduced pressure on a rotary evaporator, while keeping the bath temperature below 50 C. The resulting 1.07 kg of clear, light yellow oil was diluted with 50 mL of tap water and 400 mL of toluene and concentrated under reduced pressure on a rotary evaporator for three days, while keeping the bath temperature below 50 C. The resulting 800 g of clear, light yellow oil was diluted with 500 mL of toluene and 250 mL of IPA and concentrated under reduced pressure on a rotary evaporator for 11 days, keeping the bath temperature below 50 C. The resulting 713 g of clear, light yellow oil was titrated at 81 wt % (580 g, 91.1% yield) containing 7.9 wt % water and 7.5 wt % IPA.
With resin; In water; at 20℃; for 96h; Isethionic acid was prepared from its sodium salt by ion exchange chromatography. Isethionic acid sodium salt (105.5 mg) in water (5 mL) was added to the washed resin (2.5 g), and the mixture was stirred at ambient temperature for 4 days. The mixture was filtered, and the resin was washed with water (about 4 mL). The filtrate was added to a 10 mL volumetric flask and filled to the mark with water affording about 0.07M isethionic acid solution.
  • 71
  • [ 107-36-8 ]
  • [ 4756-75-6 ]
  • μ-oxo-bis(triphenylantimony isethionate) [ No CAS ]
  • 72
  • [ 35952-85-3 ]
  • [ 107-36-8 ]
  • ((C6H5)3BiO3SCH2CH2OH)2O [ No CAS ]
  • 73
  • [ 102614-53-9 ]
  • [ 107-36-8 ]
  • μ-oxo-bis(triphenylantimony isethionate) [ No CAS ]
  • 74
  • [ 107-36-8 ]
  • [ 19727-41-4 ]
  • [ 119987-82-5 ]
  • 75
  • [ 119987-83-6 ]
  • [ 107-36-8 ]
  • {(C6H5CH2)3SbO3SCH2CH2OH}2O [ No CAS ]
  • 76
  • [ 107-36-8 ]
  • [ 13371-35-2 ]
  • [ 104316-50-9 ]
  • 78
  • [ 107-36-8 ]
  • [ 19727-41-4 ]
  • 3CH3(1-)*Sb(5+)*2O3SCH2CH2OH(1-)=(CH3)3Sb(O3SCH2CH2OH)2 [ No CAS ]
  • 79
  • [ 107-36-8 ]
  • triphenylbismuth carbonate [ No CAS ]
  • [ 112100-71-7 ]
  • 80
  • [ 107-36-8 ]
  • triphenylbismuth carbonate [ No CAS ]
  • [ 112100-72-8 ]
  • 81
  • [ 107-36-8 ]
  • N-(3-ethynylphenylamino)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine [ No CAS ]
  • N-(3-ethynylphenylamino)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine 2-hydroxy-ethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; at 5 - 60℃; for 36 - 39h;Product distribution / selectivity; About 1 g of Erlotinib free base was weighted in a 50 mL glass reactor in the Mettler Toledo ultiMax"7 device equipped with mechanical stirring. To the free base 2- hydroxy-ethanesulfonic acid (isethionic acid) was added in a ratio of 1.1 with respect to the free base of Erlotinib. Subsequently, ethylacetate was added to a final concentration of approximately 50 mg/mL of Erlotinib free base. The reactor was heated from rT to 60oC with a rate of 1 oC/min and kept at 60oC for 60 minutes. Subsequently the reactor was allowed to cool to 5oC at rate of 1"C hr and kept at 5oC for 35-38 hr. Stirring speed during the temperature profile was 300 rpm. Solid material was obtained by filtration under vacuum with a 5 muetaiota filter. The solids were dried at 20 -25 oC at 200 mbar for approximately 1 day and additionally at 40oC and 200 mbar for about 4 - 5 h. Subsequently, the solids were dispensed in water and the resulting slurry was stirred at room temperature for at least 1 day and up till 5 days. Solid material was separated from water, dried as mentioned above and analyzed by XRPD and additional analytical methods. Analytical data are presented in Figures 3A - 3F.
  • 82
  • [ 107-36-8 ]
  • (5R)-5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)-1,3-thiazolidine-2,4-dione O,O'-dibenzoyltartrate [ No CAS ]
  • (5R)-5-(4-(2-(5-ethylpyridin-2-yl)ethoxy)benzyl)-1,3-thiazolidine-2,4-dione 2-hydroxyethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; at 45℃;Inert atmosphere; 5R)-5-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]benzyl}-1 ,3-thiazolidine-2,4-dione (-)-Omicron,Omicron'- dibenzoyl-L-tartrate (98.07% d.e.) (2.7g, 3.78mmol) was added to a solution of hydroxy-ethanesulfonic acid (1.19g) in I PA (27ml_) at 45C. Heating was stopped and isopropyl acetate (60mL) was added to the stirred solution to give some solid which was removed by filtration. The solids were collected by filtration after 1 h, washed with isopropyl acetate and dried in vacuo at 35C for 64h to give the title compound (1.28g). (Method 3) 98.56%, Rt 15.57min.; 1.44%, Rt 17.78min.; d.e. 97.12 %. LCMS (Method 6) Rt 2.86min, m/z 357 [(M- hydroxy-ethanesulfonic acid )H+], 99.4%. DSC 106C. 1H NMR (400 MHz, DMSO- /6): delta 1.23 ( 3H, t, J 8 Hz), 2.61 (2H, t, J 8 Hz), 2.77 (2H, q, J 8 Hz), 3.05 (1 H, dd, J 12, 16 Hz), 3.29 (1 H, dd, J 4, 16 Hz), 3.40 (2H, t, J 8 Hz), 3.62 (2H, t, J = 4 Hz), 4.35 (2H, t, J = 4 Hz), 4.86 (1 H, dd, J = 4, 8 Hz), 6.86 (2H, d, J 8 Hz), 7.15 (2H, d, J = 8 Hz), 7.94 (1 H, J 8 Hz), 8.33-8.40 (1 H, m), 8.70- 8.73 (1 H, m), 1 1.98 (1 H, br s).Figure 7 provides an illustrative XRPD pattern of (R)-5-{4-[2-(5-Ethyl-pyridin-2-yl)- ethoxy]-benzyl}-thiazolidine-2,4-dione 2-hydroxy-ethanesulfonic acid .The main diffraction peaks and relative intensities for the peaks shown in Figure 7 are listed in Table 7.
  • 83
  • [ 107-36-8 ]
  • [ 1207456-01-6 ]
  • [ 1373329-50-0 ]
YieldReaction ConditionsOperation in experiment
98% In tetrahydrofuran; ethanol; at 40℃;Product distribution / selectivity; The following example provides the preparation and characterization of(8^,9i?)-fluoro-8-(4-fluorophenyl)-9-(l-methyl-lH-l,2,4-triazol-5-yl)-8,9-dihydro-2H- pyrido[4,3,2-
  • 84
  • [ 107-36-8 ]
  • [ 1207456-01-6 ]
  • (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one isethionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In tetrahydrofuran; ethanol; at 40℃; [00402] Salt forms of (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-( l -methyl-l H- l ,2,4-triazoi-5-yl)-8,9- dihydro-2H-pyrido[4,3,2-Je]phthalazin-3(7 )-one were prepared by treating the compound under a given condition with an acid. Salts forms, nos. 1-18, are identified in Table 1 below, where the acid used to treat (8S,9/?)-5-fiuoro-8-(4-fluorophenyl)-9-( l -methyl- lH- l ,2,4-triazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2- i/t']phthalazin-3(7//)-one are provided in the column under "Acid," and the conditions used during treatment are provided in the column under "'Condition."
  • 85
  • [ 107-36-8 ]
  • [ 81-25-4 ]
  • [ 59893-95-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; for 1h;Reflux; Conjugation of cholate to the sulfonic acid alkyl linker by an ester was prepared following established protocols for Fischer esterification (e.g., Fischer, E. and A. Speier. 1895. Darstellung der Ester. Ber. 28(3):3252-3258. Indu, B., W. R. Ernst, and L. T. Gelbaum. 1993. Methanol-formic acid esterification equilibrium in sulfuric acid solutions: Influence of sodium salts. Ind. Eng. Chem. Res. 32(5):981-985.). Briefly, to a solution of cholate (1 equivalent) and hydroxy ethane sulfonic acid (4 equivalents), concentrated sulfuric acid was added dropwise and refluxed for one hour. The reaction was poured into cold diethyl ether and a precipitate formed immediately. The diethyl ether suspension was left overnight at 4 C. The precipitate was filtered, dissolved in 0.2 N NaOH/MeOH, precipitated a second time in diethyl ether, and kept at 4 C. for at least 2 hours. The crude precipitate was filtered and purified by silica gel column chromatography eluted by step gradient from 100% dichloromethane to 30% dichloromethane/EtOH. The compound structure was verified by 1H-NMR, FT-IR, and mass spectrometry.
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