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[ CAS No. 1280210-80-1 ] {[proInfo.proName]}

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Chemical Structure| 1280210-80-1
Chemical Structure| 1280210-80-1
Structure of 1280210-80-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1280210-80-1 ]

CAS No. :1280210-80-1 MDL No. :MFCD28144046
Formula : C12H15N3O5S2 Boiling Point : -
Linear Structure Formula :- InChI Key :PKMDOTHXIGJTKH-UHFFFAOYSA-N
M.W : 345.39 Pubchem ID :57518502
Synonyms :

Calculated chemistry of [ 1280210-80-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 7.0
Num. H-bond donors : 2.0
Molar Refractivity : 83.29
TPSA : 135.12 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) : -10.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.28
Log Po/w (XLOGP3) : -2.73
Log Po/w (WLOGP) : 1.7
Log Po/w (MLOGP) : 0.85
Log Po/w (SILICOS-IT) : -0.5
Consensus Log Po/w : 0.12

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.5
Solubility : 109.0 mg/ml ; 0.317 mol/l
Class : Very soluble
Log S (Ali) : 0.44
Solubility : 961.0 mg/ml ; 2.78 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.33
Solubility : 16.3 mg/ml ; 0.0471 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.0

Safety of [ 1280210-80-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1280210-80-1 ]

* 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.

  • Downstream synthetic route of [ 1280210-80-1 ]

[ 1280210-80-1 ] Synthesis Path-Downstream   1~60

  • 1
  • [ 1226781-82-3 ]
  • [ 98-11-3 ]
  • [ 1280210-80-1 ]
YieldReaction ConditionsOperation in experiment
92.3% In ethyl acetate; at 5 - 25℃; for 18h;Large scale; The benzene sulfonic acid 3.3Kg added ethyl acetate 14L clear,Circulating frozen brine bath to 5 ~ 15 ;2-Methanesulfonyl 5-tert-butoxycarbonyl- (2-hydro, 4-hydro, 6-hydro) -pyrrolo [3,4- c] pyrazole2.85Kg added ethyl acetate 14L in a clear,At 5 ~ 15 C was added dropwise to a solution of ethyl benzenesulfonate,Stir for 30 minutes,Go ice-cold bath,Stir at 25 ± 5 C for 16 hours,Centrifuge,Stir the solid with 17 L of ethyl acetate for 1.5 hours;Centrifuge,The solid was rinsed with 4 L of ethyl acetate,Wet products at -0.08MPa ~ -0.1MPa,40 C for 8 hours under vacuum to give a pale yellow solid Compound II 3.16Kg,Yield 92.3%.HPLC: 96.75%
In Isopropyl acetate; at 20 - 40℃; for 18h; Step D: 2-(Methylsulfonyl )-2.4,5 ,6-tetrahydropyrrolo 3 A-c] pyrazole benzenesulfomc acidsaltTo the product from Step C (87 g, 303 mmol) in isopropyl acetate (1 L) was added benzensulfonic acid (71.8 g, 454 mmol) and the mixture warmed to 40 C and stirred for 2 h. The mixture was cooled to ambient temperature and stirred for 16 h to give an off-white slurry. The solid was filtered, washed with isopropyl acetate, and suction dried to afford the title compound as a white solid. LC/MS: 188.1 (M+l).
In Isopropyl acetate; at 20 - 40℃; for 18h; To the product from Step C (87 g, 303 mmol) in isopropyl acetate (1 L) was added benzensulfonic acid (71.8 g, 454 mmol) and the mixture warmed to 40 C and stirred for 2 h. The mixture was cooled to ambient temperature and stirred for 16 h to give an off-white slurry. The solid was filtered, washed with isopropyl acetate, and suction dried to afford the title compound as a white solid. LC MS: 188.1 (M+l).
In Isopropyl acetate; at 20 - 40℃; for 18h; Step D: 2-(Methylsi^fonvn-2,4 ,6-tetrahydropYrrolo 3,4-c1pyrazole benzenesulfonic acid saltTo the product from Step C (87 g, 303 mmol) in isopropyl acetate (1 L) was added benzensulfonic acid (71.8 g, 454 mmol) and the mixture warmed to 40 C and stirred for 2 h. The mixture was cooled to ambient temperature and stirred for 16 h to give an off white slurry. The solid was filtered, washed with isopropyl acetate, and suction dried to afford the title compound as a white solid. LC/MS: 188.1 (M+l).
In Isopropyl acetate; at 0 - 20℃;Large scale; Step F: 2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate To a solution of tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate (32.1 kg, 111 mol) in iso-propylacetate (289 kg) was added benzenesulfonic acid (35.35 kg, 223 mol). The reaction was stirred for 3 days at room temperature and then cooled to 0-10 C. and stirred an additional 1 h. The resulting slurry was filtered and the cake washed with iso-propylacetate. The solids were dried overnight under vacuum at room temperature to give 2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate.

  • 3
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]-1-(1,3-oxazol-4-ylmethyl)piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 4
  • [ 1280210-80-1 ]
  • [ 1280210-99-2 ]
  • 5
  • [ 1280210-80-1 ]
  • [ 1280208-74-3 ]
  • 6
  • [ 1280210-80-1 ]
  • [ 1280211-00-8 ]
  • 7
  • [ 1280210-80-1 ]
  • [ 1280208-75-4 ]
  • 8
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-5-[2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]-1-[(2R)-2-fluoropropyl]piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-1-[(2R)-2-fluoropropyl]-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 9
  • [ 1280210-80-1 ]
  • tert-butyl {(2R,3S,5R)-2-(2,5-difiuorophenyl)-1-[(2R)-2-fluoropropyl]-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-3-yl}carbamate bis(trifluoroacetic acid salt) [ No CAS ]
  • 10
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-1-(2,2-difluoropropyl)-5-(2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl)piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-1-(2,2-difluoropropyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 11
  • [ 1280210-80-1 ]
  • [ 1280211-05-3 ]
  • 12
  • [ 1280210-80-1 ]
  • [ 1280211-06-4 ]
  • 13
  • [ 1280210-80-1 ]
  • 2-{(2R,3S,5R)-3-amino-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-1-yl}acetamide tris(trifluoroacetic acid salt) [ No CAS ]
  • 14
  • [ 1280210-80-1 ]
  • [ 1280211-09-7 ]
  • 15
  • [ 1280210-80-1 ]
  • {(2R,3S,5R)-3-amino-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-1-yl}acetic acid tris(trifluoroacetic acid salt) [ No CAS ]
  • 16
  • [ 1280210-80-1 ]
  • [ 1280211-10-0 ]
  • 17
  • [ 1280210-80-1 ]
  • 2-{(2R,3S,5R)-3-amino-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-1-yl}-1-[(3R)-3-fluoropyrrolidin-1-yl]ethanone tris(trifluoroacetic acid salt) [ No CAS ]
  • 18
  • [ 1280210-80-1 ]
  • tert-butyl {(2R,3S,5R)-2-(2,5-difiuorophenyl)-1-{2-[(3R)-3-fluoropyrrolidin-1-yl]-2-oxoethyl}-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-3-yl}carbamate bis(trifluoroacetic acid salt) [ No CAS ]
  • 19
  • [ 1280210-80-1 ]
  • 2-[(2R,3S,5R)-3-amino-2-(2,5-difiuorophenyl)-5-(2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl)piperidin-1-yl]-1-[(3R)-3-fluoropyrrolidin-1-yl]ethanone tris(trifluoroacetic acid salt) [ No CAS ]
  • 20
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-1-{2-[(3R)-3-fluoropyrrolidin-1-yl]ethyl}-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 21
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-5-(2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl)-1-{2-[(3R)-3-fluoropyrrolidine-1-yl]ethyl}piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 22
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-5-(2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl)-1-[2,2,2-trifluoro(2H2)ethyl]piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 23
  • [ 1280210-80-1 ]
  • [ 1280211-13-3 ]
  • 24
  • [ 1280210-80-1 ]
  • 1-{5-[(3R,5S,6R)-5-amino-6-(2,5-difiuorophenyl)piperidin-3-yl]-5,6-dihydropyrrolo[3,4-c]pyrazol-2(4H)-yl}-2-methylpropan-2-ol tris(trifluoroacetic acid salt) [ No CAS ]
  • 25
  • [ 1280210-80-1 ]
  • [ 1280211-14-4 ]
  • 26
  • [ 1280210-80-1 ]
  • [ 1280211-15-5 ]
  • 27
  • [ 1280210-80-1 ]
  • [ 1280211-16-6 ]
  • 28
  • [ 1280210-80-1 ]
  • 1-{5-[(3R,5S,6R)-5-amino-6-(2,5-difiuorophenyl)piperidin-3-yl]-5,6-dihydropyrrolo[3,4-c]pyrazol-1(4H)-yl}-2-methylpropan-2-ol tris(trifluoroacetic acid salt) [ No CAS ]
  • 29
  • [ 1280210-80-1 ]
  • [ 1280211-17-7 ]
  • 30
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-5-[2-(2-fluoro-2-methylpropyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 31
  • [ 1280210-80-1 ]
  • [ 1280210-89-0 ]
  • [ 1280210-88-9 ]
  • 32
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 33
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-5-[2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 34
  • [ 1280210-80-1 ]
  • 1-{(2R,3S,5R)-3-amino-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-1-yl}ethanone bis(trifluoroacetic acid salt) [ No CAS ]
  • 35
  • [ 1280210-80-1 ]
  • [ 1280210-95-8 ]
  • 36
  • [ 1280210-80-1 ]
  • 1-{(2R,3S,5R)-3-amino-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-1-yl}-2-(pyrazin-2-yl)ethanone tris(trifluoroacetic acid salt) [ No CAS ]
  • 37
  • [ 1280210-80-1 ]
  • [ 1280210-96-9 ]
  • 38
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]-1-(pyridine-2-ylmethyl)piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 39
  • [ 1280210-80-1 ]
  • [ 1280210-97-0 ]
  • 40
  • [ 1280210-80-1 ]
  • (2R,3S,5R)-2-(2,5-difiuorophenyl)-5-[2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]-1-[2-(1H-pyrazol-4-yl)ethyl]piperidin-3-amine tris(trifluoroacetic acid salt) [ No CAS ]
  • 41
  • [ 1280210-80-1 ]
  • [ 1280210-98-1 ]
  • 42
  • [ 1280210-80-1 ]
  • [ 1280210-86-7 ]
  • [ 1280210-87-8 ]
YieldReaction ConditionsOperation in experiment
With N,N,N,N,-tetramethylethylenediamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 64h; Step D: fe^-Butyli(2j? tS', -2-r2¾5-difluorophenyl)-5-("2-fmethylsulfonvn-2.6- dihydropyrrolo [3 ,4-c]pyrazol-5(4H)-yl]-6-oxopiperidin-3 -yl } carbamate To a solution of product from Step C (30.0 g, 66.3 mmol) and Intermediate 1 (25.2 g, 73.0 mmol) in dichloromethane (400 mL) and N,N~dimethylformamide (20 mL) was added N,N,N',N-tetramethyIethylenediamine (35.0 mL, 232 mmol) over 10 min. The mixture was warmed to ambient temperature over 30 min and stirring continued for 64 h. Saturated aqueous sodium hydrogen carbonate solution (200 mL) was added. The mixture was stirred for 10 min, the layers were separated and the aqueous phase extracted with dichloromethane (3 x 100 mL) and the combined organic phases were dried with anhydrous sodium sulfate, filtered and the solvent removed in vacuo. The crude solid was purified by column chromatography (silica gel 3 x Biotage 65i) eluting with ethyl acetate/hexane (gradient from 0% to 100%) to give the title compound as a colorless solid. LC/MS 512.2 (M +1).
  • 43
  • [ 951127-25-6 ]
  • [ 1280210-80-1 ]
  • tert-butyl {(2R.3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-dimethyl acetamide; sodium tris(acetoxy)borohydride; at 0 - 20℃; for 0.666667h; Step A: tert-Butyl { (2R.3S,5R)-2-(2,5-difluorophenyl)-5- [2-(methylsulfonyl)-2,6- dihydropyrrolo [3 ,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl } carbamateA vessel was charged with N,N-dimethylacetamide (520.6 kg), <strong>[1280210-80-1]2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate</strong> (intermediate 2, 30.0 kg, 86.8 mol), and tert-butyl [(2R,35)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3 -yl]carbamate (intermediate 1, 31.2 kg, 95.3 mol). After dissolving at room temperature, the solution was cooled to 0-10 C and sodium triacetoxyborohydride (24 kg, 113 mol) was added in four equalportions every 40 mm. The reaction was then allowed to warm to room temperature and stirred an additional 5h. The solution was then cooled to 5-15 C and water (672 kg) was added over 1- 2h. The resulting slurry was filtered and the cake washed sequentially with N,Ndimethylacetamide, twice with water, and then n-heptane. The solids were dried under vacuum at 40-60 C to give tert-butyl { (2R,3S,5R)-2-(2,5-difluorophenyl)-5 - [2-(methylsulfonyl)-2,6-dihydropyrrolo [3 ,4-cjpyrazol-5(41])-yljtetrahydro-2H-pyran-3-yl } carbamate.
  • 44
  • tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5 (4H)-carboxylate [ No CAS ]
  • [ 98-11-3 ]
  • [ 1280210-80-1 ]
YieldReaction ConditionsOperation in experiment
In Isopropyl acetate; at 20℃; for 72h; Step F: 2-(methylsulfonyl)-2,4.5 .6-tetrahydropyrrolo [3 ,4-clpyrazol-5-ium benzenesulfonateTo a solution of tert-butyl 2-(methylsulfonyl)-2,6-dihydropyrrolo [3 ,4-c]pyrazole-5 (4H)- carboxylate (32.1 kg, 111 mol) in iso-propylacetate (289 kg) was added benzenesulfonic acid(35.35 kg, 223 mol). The reaction was stirred for 3 days at room temperature and then cooled to0-10 C and stirred an additional 1 h. The resulting slurry was filtered and the cake washed with iso-propylacetate. The solids were dried overnight under vacuum at room temperature to give 2- (methylsulfonyl)-2,4,5,6-tetrahydropyrrolo [3 ,4-cjpyrazol-5-ium benzenesulfonate.
  • 45
  • [ 1280210-80-1 ]
  • [ 1226781-44-7 ]
  • 46
  • [ 1280210-80-1 ]
  • C21H21F2NO3 [ No CAS ]
  • C27H30F2N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of 11 (260 mg, 0.69 mmol) in DMAc (1 mL) was added Ml (288 mg, 0.84 mmol) followed by Ets (0.15 mL, 1.04 mmol) and stirred it for 5 minutes. AcOH (0.10 mL, 1.74 mmol) was added to the reaction mixture and continued the stirring for 30 minutes. NaBH(OAc)3 (0.44 g, 2.09 mmol) was added to the reaction mixture and continued the stirring for 2 days. The reaction mixture was quenched with NH4OH and extracted with EtOAc. Combined organics were concentrated under vacuum. Crude mixture was purified by silica gel chromatography afforded 12. XH NMR (400 MHz, CDC13): delta 7.68 (br. s., 1H), 7.36 - 7.48 (m, 1H), 7.17 - 7.30 (m, 2H), 7.05 (dt, J= 4.40, 8.80 Hz, 1H), 6.91 (d, J= 7.04 Hz, 2H), 6.69 (ddd, J= 3.08, 5.50, 8.73 Hz, 1H), 4.65 (br. s., 1H), 4.55 (br. s., 1H), 4.29 (d, J= 8.22 Hz, 1H), 4.04 (br. s., 2H), 3.59 - 3.82 (m, 2H), 3.30 (s, 3H), 2.47 (br. s., 1H), 1.93 - 2.05 (m, 1H), 1.39 (s, 9H).; Molecular Formula: C27H30F2N4O4S; LCMS purity: 84.2%; Expected: 544.2; Observed: 545.2 (M+l).
  • 47
  • [ 1280210-80-1 ]
  • [ 1544022-48-1 ]
  • [ 1544022-53-8 ]
YieldReaction ConditionsOperation in experiment
To a solution of 13 (100 mg, 0.26 mmol) in DMAc (1 mL) was added Ml (278 mg, 0.80 mmol) followed by Ets (0.1 1 mL, 0.80 mmol) and stirred it for 10 minutes. AcOH (0.07 mL, 1.3 mmol) was added to the reaction mixture and continued the stirring for 10 minutes. NaBH(OAc)3 (171 mg, 0.80 mmol) was added to the reaction mixture and continued the stirring for over night. The reaction mixture was quenched with NH4OH and extracted with EtOAc. Combined organics were concentrated under vacuum. Crude mixture was purified by silica gel chromatography afforded 14. XH NMR (400 MHz, CDC13): delta 7.76 (s, 1H), 7.39 - 7.21 (m, 5 H), 7.15 (br. s., 1 H), 7.00 (dt, J= 4.4, 9.2 Hz, 1 H), 6.96 - 6.87 (m, 1 H), 5.00 (s, 1 H), 4.76 - 4.67 (m, 1 H), 4.21 - 3.96 (m, 4 H), 3.73 - 3.58 (m, 1 H), 3.44 (dd, J= 4.4, 11.2 Hz, 1 H), 3.36 - 3.23 (m, 4 H), 2.31 - 2.15 (m, 1 H), 1.59 - 1.45 (m, 2 H), 1.20 (d, J= 5.3 Hz, 1 H), 0.92 - 0.81 (m, 1 H), 0.52 (d, J= 5.3 Hz, 1 H).; Molecular Formula: C27H28F2 4O4S; LCMS purity: 94.50%; Expected: 542.2; Observed: 543.0 (M+l).
  • 48
  • [ 1280210-80-1 ]
  • [ 1544022-48-1 ]
  • C19H22F2N4O2S*2C2HF3O2 [ No CAS ]
  • 49
  • [ 951127-25-6 ]
  • [ 1280210-80-1 ]
  • [ 1226781-44-7 ]
YieldReaction ConditionsOperation in experiment
57% Trifluoroacetic acid (0.45 mL, 6.1 mmol) was cooled to 0 C., compound 3 (100 mg, 0.30 mmol), compound 2 (111 mg, 0.32 mmol) were added, and reacted at 0-2 C. for 1 h. To the above reaction solution, N,N-dimethylacetamide (1.3 mL, 14.0 mmol), triethylamine (0.42 mL, 3.0 mmol) was slowly added, and the internal temperature was controlled not to exceed 15 C.; The reaction solution was cooled to 0 C., sodium triacetoxyborohydride (90.6 mg, 0.43 mmol) was added, and the reaction was performed at 0 to 2 C. for 5 h. Finally, the pH was adjusted to 9 with ammonia water, filtered, and the filtrate was added with water (15 mL). The ethyl ester was extracted three times (10 mL of cesium 3). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (dichloromethane:methanol (volume ratio)=20:1). Obtained product 5 (white solid, 70 mg, 0.18 mmol, yield: 57%).
  • 50
  • [ 951127-25-6 ]
  • [ 1280210-80-1 ]
  • [ 1226781-87-8 ]
YieldReaction ConditionsOperation in experiment
82.5% With sodium tris(acetoxy)borohydride; orthoformic acid triethyl ester; In N,N-dimethyl acetamide; at 5 - 50℃; for 12h;Inert atmosphere; Large scale; 2.46 kg of Compound III and 3.12 kg of Compound II were added to 15 L of N, N-dimethylacetamide, and nitrogenUnder guard,Circulating frozen saline bath to 5 ± 5 ,Added dropwise trimethyl orthoformate 2.2Kg,Sodium borohydride acetate was added in portions3.19Kg,Stirred at 5 ± 5 C for 2 hours,Heated to 50 ± 5 for about 10 hours;Circulating frozen saline bath to 5 ± 5 ,45 C below the drop in water 15L,Add Bi temperature at this temperature for 1 hour,Heated to 50 ± 5 C for 2 hours,Centrifuge,Wet product washed with water 5L three times,Wet product was added to the water 15L beating 1 hour,Centrifuge,50 C for 12 hours under vacuum.Get gray whiteSolid was added isopropyl ether 12L,Heated to 60 ± 5 ,Then add n-heptane 12L, cooled to 15 ± 5 , incubated for 1 hour,Suction filtered and dried under vacuum at 40 C for 12 hours to obtain 3.1Kg of white solid with a yield of 82.5%
With sodium tris(acetoxy)borohydride; In N,N-dimethyl acetamide; at 0 - 20℃; for 7.66667h;Large scale; Step A: tert-Butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolol[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate A vessel was charged with N,N-dimethylacetamide (520.6 kg), <strong>[1280210-80-1]2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate</strong> (intermediate 2, 30.0 kg, 86.8 mol), and tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl]carbamate (intermediate 1, 31.2 kg, 95.3 mol). After dissolving at room temperature, the solution was cooled to 0-10 C. and sodium triacetoxyborohydride (24 kg, 113 mol) was added in four equal portions every 40 min. The reaction was then allowed to warm to room temperature and stirred an additional 5 h. The solution was then cooled to 5-15 C. and water (672 kg) was added over 1-2 h. The resulting slurry was filtered and the cake washed sequentially with N,N-dimethylacetamide, twice with water, and then n-heptane. The solids were dried under vacuum at 40-60 C. to give tert-butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate.
With sodium tris(acetoxy)borohydride; In N,N-dimethyl acetamide; at 0 - 20℃; for 7.66667h;Large scale; Step A: tert-Butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolol[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate:_A vessel was charged with N,N-dimethylacetamide (520.6 kg), <strong>[1280210-80-1]2-(methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-5-ium benzenesulfonate</strong> (intermediate 2, 30.0 kg, 86.8 mol), and tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl]carbamate (intermediate 1, 31.2 kg, 95.3 mol). After dissolving at room temperature, the solution was cooled to 0-10 C. and sodium triacetoxyborohydride (24 kg, 113 mol) was added in four equal portions every 40 min. The reaction was then allowed to warm to room temperature and stirred an additional 5 h. The solution was then cooled to 5-15 C. and water (672 kg) was added over 1-2 h. The resulting slurry was filtered and the cake washed sequentially with N,N-dimethylacetamide, twice with water, and then n-heptane. The solids were dried under vacuum at 40-60 C. to give tert-butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate.
  • 51
  • [ 905274-02-4 ]
  • [ 1280210-80-1 ]
  • 52
  • [ 6573-19-9 ]
  • [ 1280210-80-1 ]
  • 54
  • C12H22N4O2 [ No CAS ]
  • [ 1280210-80-1 ]
  • 55
  • C7H14N4*ClH [ No CAS ]
  • [ 1280210-80-1 ]
  • 58
  • [ 951127-25-6 ]
  • [ 1280210-80-1 ]
  • [ 1226781-87-8 ]
  • tert-butyl ((2R,3S,5S)-2-(2,5-difluorophenyl)-5-(2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl)tetrahydro-2H-pyran-3-yl)carbamate [ No CAS ]
  • 60
  • [ 951127-25-6 ]
  • [ 1280210-80-1 ]
  • [ 1226781-44-7 ]
  • omarigliptin [ No CAS ]
YieldReaction ConditionsOperation in experiment
Compound 3 1 (101 mg, 0.31 mmol) and compound 4 3(111 mg, 0.32 mmol) were dissolved intrifluoroacetic acid (0.45 mL, 6.1 mmol) at 0 oC and stirred at 0 oC for 1 h. To the resulting solution, DMAC (1.3 mL, 14.0 mmol) and TEA (0.42 mL, 3.0 mmol) were added slowly and the internaltemperature was maintained below 15 oC. The mixture was then cooled to 0 oC, treated with STAB (91mg, 0.43 mmol), and stirred at 0-2 oC for 5 h. Eventually the pH of the reaction was brought to 9 withconc. aq. NH3, and the resulting suspension was filtered. The filtrate was diluted with water (15 mL),extracted ethyl acetate for several times. Combined organic phases were dried over Na2SO4, filtered, andconcentrated in vacuo. The residue was purified by flash column chromatography (SiO2, DCM: MeOH =20:1) to yield the product 1 (white powder, 70 mg, 0.18 mmol, 57 % based on compound 3, dr = 10:1).Analytical data was parallel to literature report.
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