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[ CAS No. 1370001-96-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1370001-96-9
Chemical Structure| 1370001-96-9
Structure of 1370001-96-9 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 1370001-96-9 ]

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Product Details of [ 1370001-96-9 ]

CAS No. :1370001-96-9 MDL No. :MFCD18733395
Formula : C11H17BN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SXLFONKXBNYYRU-UHFFFAOYSA-N
M.W :220.08 Pubchem ID :66521319
Synonyms :

Calculated chemistry of [ 1370001-96-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.64
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 63.47
TPSA : 44.24 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.59
Log Po/w (WLOGP) : 1.08
Log Po/w (MLOGP) : 0.14
Log Po/w (SILICOS-IT) : 1.26
Consensus Log Po/w : 0.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.42
Solubility : 0.841 mg/ml ; 0.00382 mol/l
Class : Soluble
Log S (Ali) : -2.13
Solubility : 1.63 mg/ml ; 0.00741 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.65
Solubility : 0.0497 mg/ml ; 0.000226 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.84

Safety of [ 1370001-96-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1370001-96-9 ]

* 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 [ 1370001-96-9 ]

[ 1370001-96-9 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 1439-09-4 ]
  • [ 73183-34-3 ]
  • [ 1370001-96-9 ]
YieldReaction ConditionsOperation in experiment
100% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 90℃;Inert atmosphere; Preparation 4A: 4-Methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine[00135] Nitrogen was bubbled into a mixture of <strong>[1439-09-4]5-bromo-4-methylpyrimidine</strong> (0.100 g, 0.578 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (0.191 g, 0.751 mmol), and potassium acetate (0.129 g, 1.316 mmol) in DMSO (2.89 mL) for 10 min. Then 1 , 1 '-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.019 g, 0.024 mmol) was added and the reaction mixture was heated at 90 C overnight. The reaction was quenched with FLO. The reaction mixture was extracted with EtOAc (3X). The organic phases were combined, dried over Na2S04, filtered, and concentrated to afford the title compound (127 mg, 100%) as a dark brown residue.
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 90℃; for 24h; Preparation 43 A: 4-Methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine[00139] Nitrogen was bubbled into a mixture of <strong>[1439-09-4]5-bromo-4-methylpyrimidine</strong> (0.100 g, 0.578 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (0.191 g, 0.751 mmol), and potassium acetate (0.129 g, 1.316 mmol) in DMSO (2.89 mL) for 10 min. Then 1 , 1 '-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.019 g, 0.024 mmol) was added and the reaction mixture was heated at 90 C overnight. After 24 h, the reaction was quenched with H20 and extracted with EtOAc (3X). The organic phases were combined, dried over Na2S04, filtered, and concentrated to afford Preparation 43A as a dark brown residue. The crude material was used without further purification. MS (ESI) : m/z = 221.2 [M+H]+. HPLC Peak tr = 1.1 1 minutes. HPLC conditions: Column:Luna CI 8 4.6x30mm 3u A: 10:90 H20:ACNNH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow.
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; at 90℃; [00765] A mixture of <strong>[1439-09-4]5-bromo-4-methylpyrimidine</strong> (470 mg, 2.72 mmol), PdCl2(dppf)2 (199 mg, 0.272 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (1035 mg, 4.07 mmol) and KOAc (800 mg, 8.15 mmol) in anhydrous dioxane (15 mL) was stirred overnight at 90C. The RM was filtered through Hyflo and the solvent was evaporated off under reduced pressure. The residue was dissolved in EtOAc, washed with brine, dried over Na2S04, filtered and the filtrate was evaporated off under reduced pressure to afford the crude title product as a dark solid. UPLC-MS (Condition 3), tR = 0.30 min, m/z = 139.0 [M+H]+, 137.1 [M-H]
  • 2
  • [ 1370001-96-9 ]
  • [ 1370002-06-4 ]
  • [ 1370001-97-0 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 90℃; for 19h; Inert atmosphere; 43B Preparation 43B: 4-(4-Methylpyrimidin-5-yl)- lH-benzo[d]imidazole[00140] A reaction flask was charged with tetrakis(triphenylphosphine)palladium(0) (0.012 g, 10.29 μιηο), 4-bromo-lH-benzo[d] imidazole, formic acid salt (0.050 g, 0.206 mmol), sodium carbonate (0.109 g, 1.029 mmol), and Preparation 43 A (0.063 g, 0.288 mmol). The mixture was stirred at room temperature for 10 min under N2, then DME (0.768 mL), EtOH (0.384 mL), and water (0.384 mL) were added sequentially. The resultant mixture was heated at 90 °C overnight. After 19 h, the reaction mixture was allowed to cool to room temperature, then quenched with water and diluted with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (3X). The organic phases were combined, dried over Na2S04, filtered, and concentrated to afford a dark brown residue. The crude material was dissolved in a minimal amount of CH2CI2 and chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (24 g column, 35 mL/min, 1-22% MeOH in CH2CI2 over 30 min, tr = 24 min) gave Preparation 43B (12.0 mg, 0.057 mmol, 27.7% yield) as a red residue. MS (ESI) : m/z = 21 1.2 [M+H]+. HPLC Peak tr = 0.73 minutes. HPLC conditions:Column:Luna C18 4.6x30mm 3u A: 10:90 H20:ACN NH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow.
  • 3
  • [ 1370001-96-9 ]
  • [ 1370001-83-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; ethanol; water / 19 h / 90 °C / Inert atmosphere 2: caesium carbonate; copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / N,N-dimethyl-formamide / 22 h / 110 °C / Inert atmosphere
  • 4
  • [ 1370001-96-9 ]
  • [ 1428881-25-7 ]
  • [ 1428879-92-8 ]
YieldReaction ConditionsOperation in experiment
7.4% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 90.0℃; for 19.0h; Example 4:[00136] A reaction flask was charged with tetrakis(triphenylphosphine)palladium(0) (5.69 mg, 4.92 muiotaetaomicron?), Preparation ID (27 mg, 0.098 mmol), sodium carbonate (41.8 mg, 0.394 mmol), and Preparation 4A (65.0 mg, 0.295 mmol). The mixture was stirred at room temperature for 10 min under N2, then DME (368 mu?), EtOH (184 muL), and water (184 muL) were added sequentially. The resultant mixture was heated at 90 C overnight. After 19 hr, the reaction mixture was allowed to cool to room temperature. The reaction was quenched with water. The reaction mixture was diluted with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (3X). The organic phases were combined, dried over Na2S04, filtered, and concentrated to afford a dark brown residue. The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5-muiotaeta particles;Guard Column: Waters XBridge C18, 19 x 10 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 methanokwater with 10-mM ammonium acetate; Mobile Phase B: 95:5 methanokwater with 10-mM ammonium acetate; Gradient: 35-100% B over 25 minutes, then a 5 -minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The material was further purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5-muiotaeta particles; Guard Column: Waters XBridge CI 8, 19 x 10 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10-mM ammonium acetate; Gradient: 25- 100% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to afford the title compounds (2.1 mg, 7.4% yield). ESI MS (M+H)+ = 288.0. HPLC Peak tr = 2.31 minutes. Purity >99%. HPLC Conditions: A.
  • 5
  • [ 1370001-96-9 ]
  • 3-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-4-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)benzamide [ No CAS ]
  • N-(4-(chlorodifluoromethoxy)phenyl)-4-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-3-(4-methylpyrimidin-5-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 130℃; for 2h; Inert atmosphere; Sealed tube; 297 Example 297 N-(4-(Chlorodifluoromethoxy)phenyl)-4-((3S,4S)-3,4-dihvdroxypyrrolidin-l-yl)-3-(4- methylpyrimidin-5-yl)benzamide [00763] 4-Methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine (Stage 297.1, 94 mg, 0.429 mmol), K2C03 (118 mg, 0.857 mmol) and Pd(PPh3)4 (33.0 mg, 0.029 mmol) were added to a solution of 3-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-4-((3S,4S)-3,4- dihydroxypyrrolidin-l-yl)benzamide (Stage 244.1, 150 mg, 0.286 mmol) in DMF (2.5 mL). at RT in a vial. The vial was evacuated / purged with argon, sealed and stirred at 130°C for 2 h. The RM was diluted in EtOAc (80 mL), washed with water (3 x 30 mL), dried over Na2S04, filtered, and the solvent was evaporated off under reduced pressure. The residue was dissolved in methanol (3 mL) and filtered through a a SPE PL-Thiol cartridge (StratoSpheres, 500 mg, nominal: 1.5 mmol), the cartridge was washed with MeOH and the solvent was evaporated off under reduced pressure to give a residue which was purified by preparative SFC (Column 2-EP, from 20% to 25% in 6 min) and by preparative HPLC. The obtained residue was treated with a aq. solution of Na2CC>3 (3 mL) and extracted twice with EtOAc (2 x 30 mL). The combined organic phases were washed with water (2 x 15 mL), dried over Na2S04, filtered, and the solvent was evaporated off under reduced pressure to afford the title product as a beige solid. HPLC (Condition 10) tR = 6.091 min, UPLC-MS (Condition 11) tR = 0.93 min, m/z = 491.1 [M+H]+; XH-NMR (400 MHz, DMSO-de) δ ppm 2.19/2.40 (s, 3 H) 2.65 - 2.78 (m, 2 H) 3.06 - 3.22 (m, 2 H) 3.80 - 3.90 (m, 2 H) 5.01 - 5.12 (m, 2 H) 6.93 (d, J=8.99 Hz, 1 H) 7.32 (d, J=8.60 Hz, 2 H) 7.70 - 7.80 (m, 1 H) 7.83 - 7.89 (d, J=8.60 Hz, 2 H) 7.91 - 7.98 (m, 1 H) 8.82 (s, 1 H) 9.05 (s, 1 H) 10.01 - 10.12 (m, 1 H).
  • 6
  • [ 1370001-96-9 ]
  • N-(4-(chlorodifluoromethoxy)phenyl)-6-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)-5-iodonicotinamide [ No CAS ]
  • N-(4-(chlorodifluoromethoxy)phenyl)-6-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)-5-(4-methylpyrimidin-5-yl)nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere; 282 Example 282 N-(4-(Chlorodifluoromethoxy)phenyl)-6-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)-5-(4-methylpyrimidin-5-yl)nicotinamide [00744] N-(4-(chlorodifluoromethoxy)phenyl)-6-((3R,4R)-3 ,4-dihydroxypyrrolidin- 1 -yl)- 5-iodonicotinamide (Stage 282.1, 100 mg, 0.190 mmol) and 4-methyl-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)pyrimidine (Stage 297.1, 62.8 mg, 0.285 mmol), Pd(Ph3P)4 (21.98 mg, 0.019 mmol) and K2CO3 (79 mg, 0.571 mmol) were added to a vial and flushed with argon. DMF (2 mL) was added and the mixture was stirred at 100°C for 2 h. The solvent was evaporated off under reduced pressure. The crude product was dissolved in MeOH, filtered through a PL-resin Si-Thiol cartridge, the cartridge was washed with MeOH and the solvent was evaporated off under reduced pressure to give a residue which was purified by preparative HPLC (Condition 14 - 25% to 55% MeCN in 20 min) and followed by preparative SFC (Column Diol, from 20% to 25% in 6 min). The purified product was lyophilized in water / min vol. MeCN to afford the title product as a white powder. UPLC-MS (Condition 3), tR = 0.86 min, m/z = 492.2/494.2 [M+H]+.
  • 7
  • [ 1370001-96-9 ]
  • [ 1314773-54-0 ]
  • C16H17N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
122 36. (2-Chloro-5-methoxyphenyl)acetonitrile (see C. Pierre and 0. Baudoin, Org. Lett. 2011, 13,1816-1819) may be dimethylated using sodium hydride and methyl iodide to provide 2-(2-chloro-5-methoxyphenyl)-2-methylpropanenitrile. Suzuki reaction with 4-methyl-5-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidine was followed by cleavage of the methyl ether with the sodium salt of ethanethiol, which afforded the requisite 2-[5-hydroxy-2-(4- methylpyrim idin-5-yl)phenyl]-2-methylpropanenitrile. Reaction with 4-chlorofu ro[3,2-c]pyrid me5 was mediated by tris(dibenzylideneacetone)dipalladium(0), tricyclohexylphosphine and cesiumcarbonate.
  • 8
  • [ 1370001-96-9 ]
  • [ 1609579-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: sodium thioethylate 3: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine
  • 9
  • [ 1370001-96-9 ]
  • [ 1609581-87-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: sodium thioethylate
  • 10
  • [ 1370001-96-9 ]
  • 6-bromo-N-(4-methylthiazol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide [ No CAS ]
  • 6-(4-methylpyrimidin-5-yl)-N-(4-methylthiazol 2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 100℃; 9.a a.
Preparation of 6-(4-methylpyrimidin-5-yl)-N-(4-methylthiazol 2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (1) a. Preparation of 6-(4-methylpyrimidin-5-yl)-N-(4-methylthiazol 2-yl)-[1,2,4]triazolo[1,5-a]pyridine-8-carboxamide (1) Compound 13 (25 mg, 0.08 mmol, 1.0 eq), 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (35.5 mg, 0.16 mmol, 2.1 eq), Pd(dppf)Cl2.CH2Cl2 (5.6 mg, 0.008 mmol, 0.1 eq), 1 M sodium carbonate solution (384 μL, 0.38 mmol, 5 eq) and DME (384 μL) were added to a small microwave vial. The vial was capped and stirred overnight at 100° C. The reaction was washed with water and brine and extracted with EtOAc (2*). The organics were combined, dried (MgSO4), and concentrated to dryness. Purification by reverse phase HPLC afforded 3.4 mg (13%) of the title compound: 1H NMR (400 MHz, DMSO-d6) δ 9.24 (s, 1H), 8.84.8.82 (m, 1H), 8.67 (d, J=1.5 Hz, 1H), 8.61-8.57 (m, 2H), 8.50 (s, 1H), 6.68 (d, J=1.0 Hz, 1H), 2.63 (d, J=3.2 Hz, 3H), 2.47 (dd, J=0.88, 5.3 Hz, 3H); ES-MS [M+1]+: 352.2.
  • 11
  • [ 1370001-96-9 ]
  • tert-butyl-4-(4-bromo-6-chloro-1-(4-fluoro-3,5-dimethylbenzyl)-1H-benzo[d]imidazol-2-yl)piperazine-1-carboxylate [ No CAS ]
  • 6-chloro-1-(4-fluoro-3,5-dimethylbenzyl)-4-(4-methylpyrimidin-5-yl)-2-(piperazin-1-yl)-1H-benzo[d]imidazole trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / ethanol; N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 2: dichloromethane / 2 h / 20 °C
  • 12
  • [ 1370001-96-9 ]
  • tert-butyl-4-(4-bromo-6-chloro-1-(4-fluoro-3,5-dimethylbenzyl)-1H-benzo[d]imidazol-2-yl)piperazine-1-carboxylate [ No CAS ]
  • 6-chloro-1-(4-fluoro-3,5-dimethylbenzyl)-4-(4-methylpyrimidin-5-yl)-2-(piperazin-1-yl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In ethanol; N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere;
  • 13
  • [ 1370001-96-9 ]
  • tert-butyl-6-(4-bromo-6-chloro-1-(4-fluoro-3,5-dimethylbenzyl)-1H-benzo[d]imidazol-2-yl)-2,6-diazaspiro[3.3]heptane-2-carboxylate [ No CAS ]
  • C26H26ClFN6*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / ethanol; N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 2: 1,4-dioxane / 2 h / 20 °C
  • 14
  • [ 1370001-96-9 ]
  • tert-butyl-6-(4-bromo-6-chloro-1-(4-fluoro-3,5-dimethylbenzyl)-1H-benzo[d]imidazol-2-yl)-2,6-diazaspiro[3.3]heptane-2-carboxylate [ No CAS ]
  • C31H34ClFN6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In ethanol; N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere;
  • 15
  • [ 1370001-96-9 ]
  • tert-butyl-6-(4-bromo-6-chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazol-2-yl)-2,6-diazaspiro[3.3]heptane-2-carboxylate [ No CAS ]
  • C24H22ClFN6*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / ethanol; N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 2: 1,4-dioxane / 2 h / 20 °C
  • 16
  • [ 1370001-96-9 ]
  • tert-butyl-6-(4-bromo-6-chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazol-2-yl)-2,6-diazaspiro[3.3]heptane-2-carboxylate [ No CAS ]
  • C29H30ClFN6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In ethanol; N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere;
  • 17
  • [ 1370001-96-9 ]
  • (S)-4-bromo-12-fluoro-7a,8,13,14-tetrahydro-7H-[1,2,4]triazolo[4',3':1,6]pyrido[3,2-b]benzofuro[4,3-fg][1,4]oxazonine [ No CAS ]
  • (S)-12-fluoro-4-(4-methylpyrimidin-5-yl)-7a,8,13,14-tetrahydro-7H-[1,2,4]triazolo[4',3':1,6]pyrido[3,2-b]benzofuro[4,3-fg][1,4]oxazonine [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate In 1,4-dioxane; water at 25 - 80℃; for 6h; 35.2 Step 2: (S)-12~fluoro-4-(4-methylpyrimidin-5-yl)-7a,8, 13, 14-tetrahydro-7H- [1, 2, 4]triazolo[4 3 I, 6/pyrido[3, ..?·/ ]benzqfuro[ 4, 3~fgj(l, 4 ]oxazonine To a solution of 4-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine (56.3 mg, 256 umol, 2.00 eq), (S)-4-bromo-12-fluoro-7a,8, 13,14-tetrahydro-7H- [l,2,4]triazolo[4,,3': l,6]pyrido[3,2-b]benzofuro[4,3-fg][l,4]oxazonine (50.0 mg, 128 umol, 1.00 eq) in dioxane (5 mL), water (0 5 mL) was added NaHCCh (53.7 mg, 639. umol, 24 9 uL, 5.00 eq), Pd(dppf)Cl2 (9.35 mg, 12.8 umol, 0.100 eq) in 25°C, then the mixture was stirred at 80°C for 6 h. LCMS showed the reaction was complete, starting material was consumed, desired target mass was detected. The mixture was concentrated under reduced pressure, dissolved in Ethyl acetate (20 mL), then filtered, the filtrate was concentrated under reduced pressure to afford crude product. The crude product was purified by prep-HPLC (column: Luna C18 100*30 5u; mobile phase: [water (0.225% FA)~ACN]; B%: 20%-50%, 12 min). (S)-12-fluoro-4- (4-methylpyrimidin-5-yl)-7a,8, 13,14-tetrahydro-7H-[l ,2,4]triazolo[4',3': l,6]pyrido[3,2- b]benzofuro[4,3-fg][l,4]oxazonine (19.8 mg, 48.2 umol, 37% yield, 98.5% purity) was obtained as a white solid ' l l NMR DMSO- · 400 MHz, 6 = ppm 9.46 (s, 1 H), 9.06 (s, 1 H), 8.76 (s, i l l ), 7.69 - 7.62 (m, 1H), 7.48 (s, 1H), 6.98 (br t, ,/= 9.4 Hz, 1H), 6.71 (br dd, J = 8.4, 3.5 Hz, 1H), 4.98 - 4.89 (m, I I I), 4.86 - 4.74 (m, IH), 4.54 (br d, 7 = 9.5 Hz, 1H), 4.52 - 4.45 (m, 1H), 4.22 (br dd, 7 = 9.4, 3.4 Hz, H I), 4.05 (br d, 7 3.5 Hz, IH), 3 95 - 3 83 (m, 1H), 2.41 (s, 3H). LCMS (ESI+): m/z 405.1 (M+H).
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