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[ CAS No. 1095824-76-2 ] {[proInfo.proName]}

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Quality Control of [ 1095824-76-2 ]

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Product Details of [ 1095824-76-2 ]

CAS No. :1095824-76-2 MDL No. :MFCD17169900
Formula : C6H5NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :LIFGFPYQXSGAQL-UHFFFAOYSA-N
M.W : 171.17 Pubchem ID :49853468
Synonyms :

Calculated chemistry of [ 1095824-76-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.27
TPSA : 95.5 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) : -6.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.96
Log Po/w (XLOGP3) : 0.83
Log Po/w (WLOGP) : 1.04
Log Po/w (MLOGP) : -0.92
Log Po/w (SILICOS-IT) : 1.75
Consensus Log Po/w : 0.73

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.63
Solubility : 4.03 mg/ml ; 0.0235 mol/l
Class : Very soluble
Log S (Ali) : -2.42
Solubility : 0.654 mg/ml ; 0.00382 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.0
Solubility : 17.2 mg/ml ; 0.1 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.48

Safety of [ 1095824-76-2 ]

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 [ 1095824-76-2 ]

* 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 [ 1095824-76-2 ]

[ 1095824-76-2 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 1095824-76-2 ]
  • [ 1095824-77-3 ]
  • [ 1095825-46-9 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 2-acetyl-1,3-thiazole-5-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In 1,2-dimethoxyethane at 10 - 35℃; for 2h; Stage #2: 5-chloro-4-(trifluoromethyl)pyridin-2-amine hydrochloride With pyridine In acetonitrile at 5 - 50℃; for 2h; 1 Synthesis of 2-acetyl-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide 2-Acetyl-1,3-thiazole-5-carboxylic acid (24.7 g), 1,2-dimethoxyethane (43 mL), N,N-dimethylformamide (0.047 g) and oxalyl chloride (17.8 g) were put into a four-necked eggplant flask (100 mL), and the mixture was stirred at room temperature for 2 hr (Reaction Solution 1). Separately, 5-chloro-4-(trifluoromethyl)pyridin-2-amine hydrochloride (30.0 g), acetonitrile (96 mL) and pyridine (30.8 g) were put into a four-necked eggplant flask (500 mL), and the mixture was cooled to about 5° C. (Reaction Solution 2). Reaction Solution 1 was added to Reaction Solution 2 at 35° C. or lower, and 1,2-dimethoxyethane (15 mL) was added thereto. The mixture was stirred at room temperature for 1 hr, warmed to about 50° C., and stirred for 1 hr. Water (210 mL) was added thereto at about 50° C., and the mixture was cooled to room temperature, and was stirred for 30 min. The crystallized substance was collected by filtration, washed with a mixed solvent of acetonitrile (22.5 mL) and water (67.5 mL), washed with water (180 mL), and dried under reduced pressure at 50° C. to give the title compound. pale-brown powder, 43.4 g, yield 96%, purity 99.0% (HPLC).
Stage #1: 2-acetyl-1,3-thiazole-5-carboxylic acid With oxalyl dichloride In 1,2-dimethoxyethane at 20 - 30℃; for 3.5h; Stage #2: 5-chloro-4-(trifluoromethyl)pyridin-2-amine hydrochloride With pyridine In 1,2-dimethoxyethane at 10 - 20℃; for 2.5h; D' Synthesis of Compound Diii. To a clean dry flask was charged 21.83 g (127.5 mmols, 1.06 eq) of 2-acetylthiazole-5-carboxylic acid (Compound Di), 40.5 mL of 1,2-dimethoxyethane, and 42.8 mg (5 mol %) of N,N-dimethylformamide under a nitrogen atmosphere. The resulting mixture was allowed to stir at 20-30° C. while 15.85 g (123.8 mmoles, 1.03 eq) of oxalyl chloride was charged dropwise over 30 minutes. The resulting reaction solution was allowed to stir for at least 3 hr at 25° C. In a separate flask was charged 28.07 g mmoles, 1 eq) of 5-chloro-4-(trifluoromethyl)pyridine-2-amine hydrochloride (Compound Dii), 87 mL of acetonitrile, and 29.1 mL of (360.3 mmoles, 2.99 eq) pyridine under a nitrogen atmosphere. The resulting solution was cooled to 10° C. with stirring. To the cooled Dii solution was added the activated Di solution dropwise over 30 minutes. The final combined solution was allowed to warm to RT, and the stirring was continued for an additional 2 hours. This solution may be used in the next step without isolation. However, Compound Diii can be isolated from the solution at this point by adding water dropwise until a thick slurry is obtained.
Stage #1: 2-acetyl-1,3-thiazole-5-carboxylic acid With oxalyl dichloride In 1,2-dimethoxyethane at 20 - 30℃; Inert atmosphere; Stage #2: 5-chloro-4-(trifluoromethyl)pyridin-2-amine hydrochloride With pyridine In 1,2-dimethoxyethane; acetonitrile at 10 - 20℃; Inert atmosphere; C To a clean dry flask was charged 21.83 g (127.5 mmols, 1.06 eq) of 2-acetylthiazole-5-carboxylic acid (ComPound Cl), 40.5 mL of 1,2- dimethoxy ethane, and 42.8 mg (5 mol %) of N,N-dimethylformamide under a nitrogen atmosphere. The resulting mixture was allowed to stir at 20-30 °C while 15.85 g (123.8 mmoles, 1.03eq) of oxalyl chloride was charged dropwise over 30 minutes. The resulting reaction solution was allowed to stir for at least 3 hr at 25 °C. In a separate flask was charged 28.07 g (120.5 mmoles, 1 eq) of 5-chloro-4-(trifluoromethyl)pyridine-2-amine hydrochloride (Compound C.2), 87 mL of acetonitrile, and 29.1 mL of (360.3 mmoles, 2.99 eq) pyridine under a nitrogen atmosphere. The resulting solution was cooled to 10 °C with stirring. To the cooled C.2 solution was added the activated Cl solution dropwise over 30 minutes. The final combined solution was allowed to warm to room temperature, and the stirring was continued for an additional 2 hours. This solution may be used in the next step without isolation. However, Compound C.3 can be isolated from the solution at this point by adding water dropwise until a thick slurry is obtained.
  • 2
  • [ 1095824-76-2 ]
  • [ 1095825-46-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 3.25 h / 20 °C / Inert atmosphere 2: pyridine / acetonitrile / 20 h / 5 - 20 °C / Inert atmosphere
  • 3
  • [ 1095824-76-2 ]
  • (E)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-2-(1-(hydroxyimino)ethyl)thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 3.25 h / 20 °C / Inert atmosphere 2: pyridine / acetonitrile / 20 h / 5 - 20 °C / Inert atmosphere 3: hydroxylamine hydrochloride / acetonitrile; water; 1,2-dimethoxyethane / 5.33 h / 60 °C / Inert atmosphere
  • 4
  • [ 1095824-76-2 ]
  • [ 1095823-56-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 3.25 h / 20 °C / Inert atmosphere 2: pyridine / acetonitrile / 20 h / 5 - 20 °C / Inert atmosphere 3: hydroxylamine hydrochloride / acetonitrile; water; 1,2-dimethoxyethane / 5.33 h / 60 °C / Inert atmosphere 4: zinc; acetic acid; water / butan-1-ol / 3 h / 0 - 20 °C / Inert atmosphere
  • 5
  • [ 1095824-76-2 ]
  • N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-2-(1-(5-chloro-6-(prop-2-yn-1-ylamino)pyrimidine-4-carboxamido)ethyl)thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 3.25 h / 20 °C / Inert atmosphere 2: pyridine / acetonitrile / 20 h / 5 - 20 °C / Inert atmosphere 3: hydroxylamine hydrochloride / acetonitrile; water; 1,2-dimethoxyethane / 5.33 h / 60 °C / Inert atmosphere 4: zinc; acetic acid; water / butan-1-ol / 3 h / 0 - 20 °C / Inert atmosphere 5: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
  • 6
  • [ 1095824-76-2 ]
  • N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-2-(1-(5-chloro-6-(((1-(6-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)-6-oxohexyl)-1H-1,2,3-triazol-4-yl)methyl)amino)pyrimidine-4-carboxamido)ethyl)thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 3.25 h / 20 °C / Inert atmosphere 2: pyridine / acetonitrile / 20 h / 5 - 20 °C / Inert atmosphere 3: hydroxylamine hydrochloride / acetonitrile; water; 1,2-dimethoxyethane / 5.33 h / 60 °C / Inert atmosphere 4: zinc; acetic acid; water / butan-1-ol / 3 h / 0 - 20 °C / Inert atmosphere 5: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 6: copper(ll) sulfate pentahydrate; sodium ascorbate / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere
  • 7
  • [ 1095824-76-2 ]
  • C6H4ClNO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide In 1,2-dimethoxyethane at 20℃; for 3.25h; Inert atmosphere; 94.III Step III, Synthesis of 2-acetyl-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)thiazole-5- carboxamide To a stirred mixture of 2-acetylthiazole-5-carboxylic acid (1.64 g, 9.10 mmols) in DME (3.0 mL) was added catalytic amount of DMF (3.2 uL, 0.041 mmol, one drop) under argon atmosphere. To this was added oxalyl chloride (759 uL, 8.84 mmol) in dropwise at rt over a period of 15 min, and stirred for 3 h. The resultant acid chloride was added over 10 min to a cold (5° C) stirred mixture of 5-chloro-4-(trifluoromethyl)pyridin-2-amine hydrochloride (2.00 g, 8.58 mmol) in acetonitrile (6.0 mL) and pyridine (2.08 mL, 25.7 mmol), slowly warmed up to rt, stirred for 20 h. Water and EtOAc were added and the phases were separated. The aqueous layer was extracted twice with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated. The residue was absorbed on the Celite using 5: 1 mixture of DGVLMeOH, purified by flash chromatography on silica gelcartridge using a gradient of EtOAc in DCM (0-100%) to afford white solid, which was washed with water (3 X 50 mL), and dried under vacuum to afford the title compound. (2.44 g, 73%, 90% estimated purity) as a white solid. NMR (600 MHz, MeOD) δ 8.77 (s, 1H), 8.69 (s, 1H), 8.65 (s, 1H), 2.77 (s, 3H). LRMS (m/z) calculated, 348.99; found 350.5 (M+H)+.
  • 8
  • [ 1095824-76-2 ]
  • (E)-2-(1-(2-benzoylhydrazono)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 60 °C / Inert atmosphere
  • 9
  • [ 1095824-76-2 ]
  • (E)-2-(1-(benzylimino)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / toluene / 2 h / 90 °C / Inert atmosphere
  • 10
  • [ 1095824-76-2 ]
  • (E)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-2-(1-((4-methoxybenzyl)imino)ethyl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / toluene / 2 h / 85 °C / Inert atmosphere
  • 11
  • [ 1095824-76-2 ]
  • (E)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-2-(1-((4-methoxyphenyl)imino)ethyl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: toluene-4-sulfonic acid / toluene / 18 h / 90 °C / Inert atmosphere
  • 12
  • [ 1095824-76-2 ]
  • 2-((1S)-1-(2-benzoylhydrazinyl)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 60 °C / Inert atmosphere 3.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; C36H35F12FeP2; hydrogen / methanol / 20 h / 50 °C / 7500.75 Torr / Schlenk technique; Autoclave
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 60 °C / Inert atmosphere 3.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; potassium <i>tert</i>-butylate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; hydrogen / methanol / 16 h / 50 °C / 37503.8 Torr / Autoclave
  • 13
  • [ 1095824-76-2 ]
  • (E)-2-(1-(benzhydrylimino)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux
  • 14
  • [ 1095824-76-2 ]
  • 2-((1R)-1-aminoethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide (S)-mandelate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / toluene / 2 h / 50 °C / 22502.3 Torr / Autoclave 4.1: N-Bromosuccinimide; triethylamine / acetonitrile; water / 18 h / 10 - 35 °C 4.2: 20 °C
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine / dichloromethane / 0.17 h / Autoclave 3.2: 23 h / 50 °C / Autoclave 4.1: N-Bromosuccinimide; triethylamine / acetonitrile; water / 18 h / 10 - 35 °C 4.2: 20 °C
  • 15
  • [ 1095824-76-2 ]
  • [ 1095823-62-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: ammonium salicylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-PTBP-Skewphos / tetrahydrofuran / 1.5 h / 40 °C / Autoclave 2.2: 24 h / 40 °C / 37503.8 Torr / Autoclave
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: ammonium salicylate; bis(1,5-cyclooctadiene)iridium(I) tetrafluoroborate; (R,R)-PTBP-Skewphos / tetrahydrofuran / 2 h / 50 °C 2.2: 20 h / 50 °C / 22502.3 Torr
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: ammonium salicylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-PTBP-Skewphos; N-benzyl-N,N,N-triethylammonium chloride; hydrogen / isopropyl alcohol / 22 h / 50 °C / 22502.3 Torr / Autoclave
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; ammonium salicylate; C39H39FeNP2; hydrogen / tetrahydrofuran / 22 h / 50 °C / 22502.3 Torr
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / toluene / 2 h / 50 °C / 22502.3 Torr / Autoclave 4.1: triethylsilane; aluminum (III) chloride / 23 h / 80 °C / Schlenk technique
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine / dichloromethane / 0.17 h / Autoclave 3.2: 23 h / 50 °C / Autoclave 4.1: triethylsilane; aluminum (III) chloride / 23 h / 80 °C / Schlenk technique
Multi-step reaction with 5 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / toluene / 2 h / 50 °C / 22502.3 Torr / Autoclave 4.1: N-Bromosuccinimide; triethylamine / acetonitrile; water / 18 h / 10 - 35 °C 4.2: 20 °C 5.1: sodium hydrogencarbonate / acetonitrile; water / 0.25 h / 10 - 35 °C
Multi-step reaction with 5 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine / dichloromethane / 0.17 h / Autoclave 3.2: 23 h / 50 °C / Autoclave 4.1: N-Bromosuccinimide; triethylamine / acetonitrile; water / 18 h / 10 - 35 °C 4.2: 20 °C 5.1: sodium hydrogencarbonate / acetonitrile; water / 0.25 h / 10 - 35 °C

  • 16
  • [ 1095824-76-2 ]
  • 6-amino-5-chloro-N-[(1R)-1-[5-[[[5-chloro-4-(trifluoromethyl)-2-pyridinyl]amino]carbonyl]-2-thiazolyl]ethyl]-4-pyrimidinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: ammonium salicylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-PTBP-Skewphos / tetrahydrofuran / 1.5 h / 40 °C / Autoclave 2.2: 24 h / 40 °C / 37503.8 Torr / Autoclave 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 4 h / 10 - 35 °C
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: ammonium salicylate; bis(1,5-cyclooctadiene)iridium(I) tetrafluoroborate; (R,R)-PTBP-Skewphos / tetrahydrofuran / 2 h / 50 °C 2.2: 20 h / 50 °C / 22502.3 Torr 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 4 h / 10 - 35 °C
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: ammonium salicylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-PTBP-Skewphos; N-benzyl-N,N,N-triethylammonium chloride; hydrogen / isopropyl alcohol / 22 h / 50 °C / 22502.3 Torr / Autoclave 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 4 h / 10 - 35 °C
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; ammonium salicylate; C39H39FeNP2; hydrogen / tetrahydrofuran / 22 h / 50 °C / 22502.3 Torr 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 4 h / 10 - 35 °C
Multi-step reaction with 5 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / toluene / 2 h / 50 °C / 22502.3 Torr / Autoclave 4.1: triethylsilane; aluminum (III) chloride / 23 h / 80 °C / Schlenk technique 5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 4 h / 10 - 35 °C
Multi-step reaction with 5 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine / dichloromethane / 0.17 h / Autoclave 3.2: 23 h / 50 °C / Autoclave 4.1: triethylsilane; aluminum (III) chloride / 23 h / 80 °C / Schlenk technique 5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 4 h / 10 - 35 °C
Multi-step reaction with 6 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / toluene / 2 h / 50 °C / 22502.3 Torr / Autoclave 4.1: N-Bromosuccinimide; triethylamine / acetonitrile; water / 18 h / 10 - 35 °C 4.2: 20 °C 5.1: sodium hydrogencarbonate / acetonitrile; water / 0.25 h / 10 - 35 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 4 h / 10 - 35 °C
Multi-step reaction with 6 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine / dichloromethane / 0.17 h / Autoclave 3.2: 23 h / 50 °C / Autoclave 4.1: N-Bromosuccinimide; triethylamine / acetonitrile; water / 18 h / 10 - 35 °C 4.2: 20 °C 5.1: sodium hydrogencarbonate / acetonitrile; water / 0.25 h / 10 - 35 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl acetamide / 4 h / 10 - 35 °C

  • 17
  • [ 1095824-76-2 ]
  • 2-((1R)-1-(benzhydrylamino)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / toluene / 2 h / 50 °C / 22502.3 Torr / Autoclave
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine / dichloromethane / 0.17 h / Autoclave 3.2: 23 h / 50 °C / Autoclave
  • 18
  • [ 1095824-76-2 ]
  • 2-((1R)-1-aminoethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide hydrobromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / toluene / 2 h / 50 °C / 22502.3 Torr / Autoclave 4.1: N-Bromosuccinimide / water / 19 h / 80 °C
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine / dichloromethane / 0.17 h / Autoclave 3.2: 23 h / 50 °C / Autoclave 4.1: N-Bromosuccinimide / water / 19 h / 80 °C
  • 19
  • [ 1095824-76-2 ]
  • 2-((1R)-1-aminoethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / toluene / 2 h / 50 °C / 22502.3 Torr / Autoclave 4.1: N-Bromosuccinimide / dichloromethane / 3 h / 0 - 35 °C / Schlenk technique; Inert atmosphere 5.1: hydrogenchloride / acetonitrile; water; diethyl ether / 15 h / 10 - 35 °C
Multi-step reaction with 5 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine / dichloromethane / 0.17 h / Autoclave 3.2: 23 h / 50 °C / Autoclave 4.1: N-Bromosuccinimide / dichloromethane / 3 h / 0 - 35 °C / Schlenk technique; Inert atmosphere 5.1: hydrogenchloride / acetonitrile; water; diethyl ether / 15 h / 10 - 35 °C
  • 20
  • [ 1095824-76-2 ]
  • (E)-2-(1-(bis(4-methoxyphenyl)methyl)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 8 h / Inert atmosphere; Reflux
  • 21
  • [ 1095824-76-2 ]
  • (E)-(S)-tert-butyl 2-(1-(5-((5-chloro-4-(trifluoromethyl)pyridin-2-yl)carbamoyl)-1,3-thiazol-2-yl)ethylidene)hydrazinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / toluene / 2 h / 60 °C / Inert atmosphere
  • 22
  • [ 1095824-76-2 ]
  • 2-((1R)-1-((bis(4-methoxyphenyl)methyl)amino)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 8 h / Inert atmosphere; Reflux 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / dichloromethane / 24 h / 50 °C / Autoclave
  • 23
  • [ 1095824-76-2 ]
  • 2-((1R)-1-(2-benzoylhydrazinyl)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 60 °C / Inert atmosphere 3.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; potassium <i>tert</i>-butylate; hydrogen / methanol / 16 h / 50 °C / 37503.8 Torr / Autoclave
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 60 °C / Inert atmosphere 3.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; potassium <i>tert</i>-butylate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; hydrogen / methanol / 16 h / 50 °C / 37503.8 Torr / Autoclave
  • 24
  • [ 1095824-76-2 ]
  • 2-((1R)-1-aminoethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide hydrochloride [ No CAS ]
  • 2-((1S)-1-aminoethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 60 °C / Inert atmosphere 3.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; C36H35F12FeP2; hydrogen / methanol / 20 h / 50 °C / 7500.75 Torr / Schlenk technique; Autoclave 4.1: zinc; chloro-trimethyl-silane / methanol / 17 h / 20 °C / Schlenk technique
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: toluene-4-sulfonic acid / methanol / 1 h / 60 °C / Inert atmosphere 3.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; potassium <i>tert</i>-butylate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; hydrogen / methanol / 16 h / 50 °C / 37503.8 Torr / Autoclave 4.1: zinc; chloro-trimethyl-silane / methanol / 17 h / 20 °C / Schlenk technique
  • 25
  • [ 1095824-76-2 ]
  • tert-butyl 2-((1S)-1-(5-((5-chloro-4-(trifluoromethyl)pyridin-2-yl)carbamoyl)-1,3-thiazol-2-yl)ethyl)hydrazinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / toluene / 2 h / 60 °C / Inert atmosphere 3.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; C48H50P2; hydrogen / isopropyl alcohol / 15 h / 50 °C / 7500.75 Torr / Autoclave
  • 26
  • [ 1095824-76-2 ]
  • (R)-2-(1-(benzylamino)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide [ No CAS ]
  • (S)-2-(1-(benzylamino)ethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / toluene / 2 h / 90 °C / Inert atmosphere 3.1: (R,R)-(−)-2,3-bis(t-butylmethylphosphino)quinoxaline; chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen / methanol / 2 h / 50 °C / 37503.8 Torr / Autoclave
  • 27
  • [ 1095824-76-2 ]
  • (R)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-2-(1-((4-methoxybenzyl)amino)ethyl)-1,3-thiazole-5-carboxamide [ No CAS ]
  • (S)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)-2-(1-((4-methoxybenzyl)amino)ethyl)-1,3-thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / toluene / 2 h / 85 °C / Inert atmosphere 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine ethanol; hydrogen / tetrahydrofuran / 2 h / 50 °C / 22502.3 Torr / Autoclave
  • 28
  • [ 1095824-76-2 ]
  • C25H18ClF3N4OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / toluene / 2 h / 50 °C / 22502.3 Torr / Autoclave 4.1: N-Bromosuccinimide / dichloromethane / 3 h / 0 - 35 °C / Schlenk technique; Inert atmosphere
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine / dichloromethane / 0.17 h / Autoclave 3.2: 23 h / 50 °C / Autoclave 4.1: N-Bromosuccinimide / dichloromethane / 3 h / 0 - 35 °C / Schlenk technique; Inert atmosphere
  • 29
  • [ 1095824-76-2 ]
  • C25H20ClF3N4OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: C66H64Cl2N2P2Ru; hydrogen / 2 h / 50 °C / 22502.3 Torr / Autoclave
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: acetic acid / ethanol / 6.5 h / Dean-Stark; Reflux 3.1: (S)-N,N-dimethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine; hydrogen / toluene / 2 h / 50 °C / 22502.3 Torr / Autoclave
  • 30
  • [ 1095824-76-2 ]
  • [ 1095825-44-7 ]
  • C12H9ClF3N3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; ammonium salicylate; C39H39FeNP2; hydrogen / tetrahydrofuran / 22 h / 50 °C / 22502.3 Torr
  • 31
  • [ 1095824-76-2 ]
  • [ 1095825-44-7 ]
  • C12H9ClF3N3O2S [ No CAS ]
  • C24H15Cl2F6N7O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: ammonium salicylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-PTBP-Skewphos / tetrahydrofuran / 1.5 h / 40 °C / Autoclave 2.2: 24 h / 40 °C / 37503.8 Torr / Autoclave
  • 32
  • [ 1095824-76-2 ]
  • C12H9ClF3N3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: ammonium salicylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-PTBP-Skewphos; N-benzyl-N,N,N-triethylammonium chloride; hydrogen / isopropyl alcohol / 22 h / 50 °C / 22502.3 Torr / Autoclave
  • 33
  • [ 1095824-76-2 ]
  • C12H9ClF3N3O2S [ No CAS ]
  • C24H15Cl2F6N7O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 1,2-dimethoxyethane / 2 h / 10 - 35 °C 1.2: 2 h / 5 - 50 °C 2.1: ammonium salicylate; bis(1,5-cyclooctadiene)iridium(I) tetrafluoroborate; (R,R)-PTBP-Skewphos / tetrahydrofuran / 2 h / 50 °C 2.2: 20 h / 50 °C / 22502.3 Torr
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