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[ CAS No. 1350821-95-2 ]

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Product Details of [ 1350821-95-2 ]

CAS No. :1350821-95-2 MDL No. :MFCD26727798
Formula : C10H16O3 Boiling Point : -
Linear Structure Formula :- InChI Key :SUBCPWAUFQPRLU-UHFFFAOYSA-N
M.W :184.23 g/mol Pubchem ID :83854307
Synonyms :

Safety of [ 1350821-95-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1350821-95-2 ]

* 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 [ 1350821-95-2 ]

[ 1350821-95-2 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 1350821-95-2 ]
  • [ 1350822-05-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / -10 - 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; <i>tert</i>-butyl alcohol / acetonitrile / 1.5 h / 70 °C
0.047 g With diethylamino-sulfur trifluoride In dichloromethane at -78 - 22℃; for 1h; Intermediate A138B: Methyl 4-(fluoromethyl)bicyclo[2.2.1]heptane-1-carboxylate Intermediate A138B: Methyl 4-(fluoromethyl)bicyclo[2.2.1]heptane-1-carboxylate A solution of Intermediate A138A (0.155 g, 0.841 mmol) in DCM (5 mL), was cooled to -78° C. DAST (0.111 mL, 0.841 mmol) was added and the reaction mixture was stirred at 22° C. for 1 h. The reaction mixture was quenched at 0° C. by the careful addition of a saturated aq. solution of NaHCO3. The reaction mixture was diluted with DCM. The organic layer was separated and the aqueous phase was extracted twice more with DCM. The combined organic phases were dried over MgSO4 and concentrated under reduced pressure. The crude reaction mixture was purified by silica gel chromatography (24 g REDISEP column, eluting with a gradient from 0-30% EtOAc in hexanes).
  • 2
  • [ 1350821-95-2 ]
  • [ 1350821-85-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / -10 - 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; <i>tert</i>-butyl alcohol / acetonitrile / 1.5 h / 70 °C 3: potassium hydroxide / methanol / Reflux
  • 3
  • [ 1350821-95-2 ]
  • [ 1350821-89-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: pyridine / dichloromethane / -10 - 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; <i>tert</i>-butyl alcohol / acetonitrile / 1.5 h / 70 °C 3: potassium hydroxide / methanol / Reflux 4: thionyl chloride / acetonitrile / 70 °C / Inert atmosphere 5: triethylamine / acetonitrile / 1 h / 20 °C
  • 4
  • [ 1350821-95-2 ]
  • C9H12ClFO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine / dichloromethane / -10 - 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; <i>tert</i>-butyl alcohol / acetonitrile / 1.5 h / 70 °C 3: potassium hydroxide / methanol / Reflux 4: thionyl chloride / acetonitrile / 70 °C / Inert atmosphere
  • 5
  • [ 1350821-95-2 ]
  • C35H44F2N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: pyridine / dichloromethane / -10 - 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; <i>tert</i>-butyl alcohol / acetonitrile / 1.5 h / 70 °C 3: potassium hydroxide / methanol / Reflux 4: thionyl chloride / acetonitrile / 70 °C / Inert atmosphere 5: triethylamine / acetonitrile / 0.5 h / 20 °C
  • 6
  • [ 1350821-95-2 ]
  • [ 1350821-94-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: pyridine / dichloromethane / -10 - 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; <i>tert</i>-butyl alcohol / acetonitrile / 1.5 h / 70 °C 3: potassium hydroxide / methanol / Reflux 4: thionyl chloride / acetonitrile / 70 °C / Inert atmosphere 5: triethylamine / acetonitrile / 0.5 h / 20 °C 6: water; sodium hydrogencarbonate / methanol / 2 h / 50 °C
  • 7
  • [ 358-23-6 ]
  • [ 1350821-95-2 ]
  • [ 1350821-98-5 ]
YieldReaction ConditionsOperation in experiment
77% With pyridine In dichloromethane at -10 - 20℃; Inert atmosphere; 3. General procedure for synthesis of compounds 3a, 3c and 3d (LG = Triflate). General procedure: In a flame dried three-neck flask under argon atmosphere, alcohol 2 was dissolved in CH2Cl2 at room temperature. Pyridine was added to the solution via syringe and the reaction mixture was cooled to -10 oC with ice/ MeOH bath. Triflic anhydride was added dropwise to the reaction mixture in a way that the temperature remained below -2 oC. Upon completion of the addition, the reaction mixture was stirred for 1 hour at -10 oC, and thereafter was stirred further for 6-8 hours at room temperature, quenched with water and stirred for 15 minutes at room temperature. The organic phase was washed with 0.2 N HCl, water and brine. The organic phase was collected, dried (Na2SO4) and concentrated under vacuo to dryness.
  • 9
  • [ 15448-77-8 ]
  • [ 1350821-95-2 ]
YieldReaction ConditionsOperation in experiment
90% With dimethylsulfide borane complex In tetrahydrofuran at 20℃; 1.D1.2 Step 2: Synthesis of methyl 4-(hydroxymethyl)bicyclo[2.2.1]heptane-1-carboxylate Under ice bath, In a single-neck flask containing 4-(carbomethoxy)bicyclo[2.2.1]heptane-1-carboxylic acid (4.17 g, 21.03 mmol), dry tetrahydrofuran (100 mL) was added. Borane dimethyl sulfide complex (2.7 mL, 27.35 mmol, 10.0 M) was slowly added dropwise using a syringe. After the dropwise addition was completed, the mixture was stirred at room temperature overnight. Methanol (10 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 4 hours to quench. Ethyl acetate/water extraction, the organic phase was washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated and separated by column chromatography (petroleum ether/ethyl acetate=3:2) to obtain methyl 4-(hydroxylmethyl)bicyclo[2.2.1]heptane-1-carboxylate (3.53 g, 90% yield).
89.12% With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 16h; 8 Intermediate: Preparation of 4-(methoxymethyl)bicyclo[2.2.1]heptane-1-carbaldehyde I-8d Commercially available I-8d1 (60.00g, 302.70mmol, 1.0eq) was dissolved in THF (0.6L) and placed in a four-necked flask, under nitrogen protection, cooled to 0-10°C, BH 3-Me 2S was added dropwise (60.5mL, 2.0eq). During the dropwise addition, the temperature did not change significantly, but there was obvious outgassing. After dripping, the temperature was naturally raised to room temperature 20 °C, and the reaction was stirred overnight for 16 h. TLC showed complete reaction of starting material. Cool down to 0-10 °C, add saturated NH 4 Cl solution dropwise, and stir for 1 h after the dropping is completed. The system separated and the aqueous phase TLC monitored almost no product and was discarded. The organic phase was dried over magnesium sulfate and evaporated to dryness. After the crude product was separated by silica gel column chromatography (PE/EA(v/v)=20/110/1), a yellowish liquid I-8d2 (49.70 g, yield 89.12%) was obtained.
70% Stage #1: 4-carbomethoxybicyclo<2.2.1>heptane-1-carboxylic acid With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With lithium hydroxide monohydrate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; 2. General procedure for synthesis of compounds 2a-d. General procedure: In flame dried three-necked flask under argon atmosphere, the appropriate acid was dissolved in freshly distilled THF. This reaction mixture was cooled to 0 oC, 2 M borane dimethyl sulphide in THF was added dropwise and the reaction mixture was stirred at this temperature for 20 minutes then further stirred for 2.5 h at room temperature. This reaction mixture was quenched with water and stirred for 2 h at room temperature. The solvent was evaporated under reduced pressure and the residue was extracted with EtOAc. The organic layer was washed with saturated NaHCO3, collected, dried over anhydrous MgSO4 and evaporated in vacuo to dryness.
2.5 g With borane-THF In tetrahydrofuran at -40 - 0℃; 228.E E) Methyl 4-(hydroxymethyl)bicyd [1269] ^ Borane-tetrahydrofuran complex (1 M THF solution, 22.7 mL) was added dropwise to a solution of 4-(methoxycarbonyl)bicyclo[2.2.1]heptane-l-carboxylic acid (3.00 g) in THF (60 mL) at -40°C, the resultant was stirred for 1 hour at the same temperature, and was further stirred for 2 hours at 0°C. An aqueous saturated sodium hydrogen carbonate solution was added to the reaction mixture at 0°C, and extraction thereof was performed using ethyl acetate. The obtained organic layer was sequentially washed with water and a saturated saline solution, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure, thereby obtaining the title compound (2.50 g). 1H NMR (400 MHz, DMSO-d^ 1.21-1.24 (2H, m), 1.42 (2H, s), 1.55-1.61 (4H, m), 1.82-1.89 (2H, m), 3.42 (2H, d, J = 5.36 Hz), 3.58 (3H, s), 4.47 (1H, t, J = 5.36 Hz).
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 18h; Sealed tube; Inert atmosphere; Intermediate A138A: Methyl 4-(hydroxymethyl)bicyclo[2.2.1]heptane-1-carboxylate Intermediate A138A: Methyl 4-(hydroxymethyl)bicyclo[2.2.1]heptane-1-carboxylate Intermediate A138A was prepared following the synthetic route described in Scheme 97. The experimental procedures described in Eur. J Med. Chem., 46:5728-5735 (2011) were followed. A flask charged with a solution of Intermediate A137D (316 mg, 1.594 mmol) in THF (8 mL) was sealed with a septum and purged with dry N2. The solution was cooled to 0° C. prior to the dropwise addition of a 2.0 M solution of borane-methyl sulfide complex (0.996 mL, 1.993 mmol) in THF. The reaction mixture was allowed to gradually warm to RT. After 18 h, MeOH (5 mL) was added to the reaction and the mixture was heated to reflux for 2 h. The solution was then cooled to RT, concentrated under reduced pressure and diluted with equal parts EtOAc and water. The organic phase was separated and the aqueous phase was extracted twice more with EtOAc. The combined organic layers were washed twice with a 1 N aq.
With borane-THF In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; 85.1 Step 1: 143-2 To a mixture of 143-1 (480 mg, 2.42 mmol) in THF (10 mL) was added Borane-tetrahydrofuran complex (1 M, 3.63 mL) at 0 under the nitrogen atmosphere dropwise. The reaction mixture was stirred for 2 hr at 25 . Them, to the reaction mixture was added MeOH (20 mL) at 025 dropwise. The reaction mixture was stirred at room temperature (25 ) for 0.5 hr and concentrated with a rotary evaporator to obtain crude 143-2 (450 mg) .

  • 10
  • [ 498-66-8 ]
  • [ 1350821-95-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: ruthenium trichloride; sodium periodate / water; ethyl acetate; acetonitrile / 2 h / 20 °C / Cooling with ice 2.1: sulfuric acid / Reflux 3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -75 - -10 °C / Inert atmosphere 3.2: 0.5 h / -75 - -70 °C / Inert atmosphere 4.1: sodium hydroxide / tetrahydrofuran; methanol / 20 °C 5.1: borane-THF / tetrahydrofuran / -40 - 0 °C
  • 11
  • cycloheptane-1,3-dicarboxylic acid [ No CAS ]
  • [ 1350821-95-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sulfuric acid / Reflux 2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -75 - -10 °C / Inert atmosphere 2.2: 0.5 h / -75 - -70 °C / Inert atmosphere 3.1: sodium hydroxide / tetrahydrofuran; methanol / 20 °C 4.1: borane-THF / tetrahydrofuran / -40 - 0 °C
  • 12
  • [ 343949-04-2 ]
  • [ 1350821-95-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -75 - -10 °C / Inert atmosphere 1.2: 0.5 h / -75 - -70 °C / Inert atmosphere 2.1: sodium hydroxide / tetrahydrofuran; methanol / 20 °C 3.1: borane-THF / tetrahydrofuran / -40 - 0 °C
  • 13
  • [ 1350821-95-2 ]
  • methyl 4-formylbicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With Dess-Martin periodane In dichloromethane at 20℃; for 18h; Intermediate A139A: Methyl 4-formylbicyclo[2.2.1]heptane-1-carboxylate Intermediate A139A: Methyl 4-formylbicyclo[2.2.1]heptane-1-carboxylate To a solution of Intermediate A138A (0.118 g, 0.640 mmol) in DCM (5 mL) was added Dess-Martin periodinane (0.326 g, 0.769 mmol). The reaction mixture was allowed to stir at RT for 18 h. The reaction was diluted with equal parts DCM and a saturated aq. solution of NaHCO3. The organic phase was separated and the aqueous phase was extracted twice more with DCM. The combined organic layers were dried over MgSO4, and concentrated to provide a white solid. The crude reaction mixture was purified by silica gel chromatography (24 g REDISEP column, eluting with a gradient from 0-15% EtOAc in hexanes).
72% With Dess-Martin periodane In dichloromethane at 20℃; 1.D1.3 Step 3: Synthesis of methyl 4-formylbicyclo[2.2.1]heptane-1-carboxylate In a single-neck flask containing methyl 4-(hydroxymethyl)bicyclo[2.2.1]heptane-1-carboxylate (4.75 g, 25.7 mmol), dichloromethane (180 mL) was added to dissolve it. Dess-Martin reagent (13.1 g, 30.9 mmol) was added. The reaction solution was stirred at room temperature, and the reaction was detected by TLC until the raw material disappeared. Celite was filtered, the filtrate was concentrated and separated by column chromatography (petroleum ether/ethyl acetate=5:1) to obtain methyl 4-formylbicyclo[2.2.1]heptane-1-carboxylate (3.38 g, yield 72%).
2.6 g With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 3h; 228.F F) Methyl 4-formylbicyclo[2.2.1 ]heptane- 1 -carboxylate [ 1270] Pyridinium chlorochromate (10.1 g) was added to a solution of methyl 4-(hydroxymethyl)bicyclo[2.2.1]heptane-l-carboxylate (4.30 g) in dichloromethane (80 mL) at 0°C, and the resultant was stirred for 3 hours at room temperature. The reaction mixture was filtered using celite, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by a silica gel column chromatography (hexane ethyl acetate), thereby obtaining the title compound (2.60 g). 1H NMR (400 MHz, DMSO-d6)6 1.44-1.49 (1H, m), 1.55-1.70 (3H, m), 1.81 (2H, s), 1.91-2.01 (4H, m), 3.60 (3H, s), 9.75 (1H, s).
With Dess-Martin periodane In dichloromethane at 20℃; for 2h; 1.6 Step 6: methyl 4-formylbicyclo[2.2.1]heptane-1-carboxylate A mixture of methyl 4-(hydroxymethyl)bicyclo[2.2.1]heptane-1-carboxylate (PharmaBlock, catNo.PBZ3820: 400 mg, 2.17 mmol) and Dess-Martin periodinane (1381 mg, 3.26 mmol) in dichloromethane (12.0 mL) was stirred at room temperature for 2 h. The reaction mixture was quenched with 20% aqueous Na2S2O3 solution and saturated aqueous NaHCO3 solution, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was used directly in the next step without further purification.
With Dess-Martin periodane In dichloromethane at 20℃; for 2h; 20.6 Step 6; methyl 4-formylbicyclo[2.2.1]heptane-1-carboxylate A mixture of methyl 4-(hydroxymethyl)bicyclo[2.2.1]heptane-1-carboxylate (PharmaBlock, cat PBZ3820: 400 mg, 2.17 mmol) and Dess-Martin periodinane (1381 mg, 3.26 mmol) in dichloromethane (12.0 mL) was stirred at room temperature for 2 h. The reaction mixture was quenched with 20% aqueous Na2S2O3 solution and saturated aqueous NaHCO3 solution, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was used directly in the next step without further purification.

  • 14
  • [ 1350821-95-2 ]
  • methyl 4-((E)-(hydroxyimino)methyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 3 h / 0 - 20 °C 2: sodium hydrogencarbonate; hydroxylamine hydrochloride / methanol / 2 h / 20 °C
  • 15
  • [ 1350821-95-2 ]
  • methyl 4-((Z)-chloro(hydroxyimino)methyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridinium chlorochromate / dichloromethane / 3 h / 0 - 20 °C 2: sodium hydrogencarbonate; hydroxylamine hydrochloride / methanol / 2 h / 20 °C 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 20 °C
  • 16
  • [ 1350821-95-2 ]
  • tert-butyl 7-(4-(methoxycarbonyl)bicyclo[2.2.1]hept-1-yl)-5-oxa-2,6-diazaspiro[3.4]oct-6-ene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridinium chlorochromate / dichloromethane / 3 h / 0 - 20 °C 2: sodium hydrogencarbonate; hydroxylamine hydrochloride / methanol / 2 h / 20 °C 3: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 20 °C 4: triethylamine / dichloromethane / 24 h / 20 °C
  • 17
  • [ 1350821-95-2 ]
  • methyl 4-(2-((2,6-diethoxy-4'-fluorobiphenyl-4-yl)methyl)-5-oxa-2,6-diazaspiro[3.4]oct-6-en-7-yl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pyridinium chlorochromate / dichloromethane / 3 h / 0 - 20 °C 2.1: sodium hydrogencarbonate; hydroxylamine hydrochloride / methanol / 2 h / 20 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 20 °C 4.1: triethylamine / dichloromethane / 24 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C 5.2: 0.17 h / 20 °C 5.3: 5 h / 20 °C
  • 18
  • [ 1350821-95-2 ]
  • 4-(2-((2,6-diethoxy-4'-fluorobiphenyl-4-yl)methyl)-5-oxa-2,6-diazaspiro[3.4]oct-6-en-7-yl)bicyclo[2.2.1]heptane-1-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pyridinium chlorochromate / dichloromethane / 3 h / 0 - 20 °C 2.1: sodium hydrogencarbonate; hydroxylamine hydrochloride / methanol / 2 h / 20 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 20 °C 4.1: triethylamine / dichloromethane / 24 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C 5.2: 0.17 h / 20 °C 5.3: 5 h / 20 °C 6.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 6 h / 20 °C
  • 19
  • [ 1350821-95-2 ]
  • methyl 4-(difluoromethyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 18 h / 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 18 h / 0 - 20 °C
  • 20
  • [ 1350821-95-2 ]
  • methyl 4-(2-(2-((2,2'-dimethyl-3'-(1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C
  • 21
  • [ 1350821-95-2 ]
  • methyl 4-(2-(2-((2,2'-dichloro-3'-(5-(4-hydroxycyclohexyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / 2 h / 20 °C
  • 22
  • [ 1350821-95-2 ]
  • methyl 4-(2-(2-((2-chloro-3'-(5-(4-hydroxycyclohexyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-2'-methyl-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C
  • 23
  • [ 1350821-95-2 ]
  • methyl 4-(2-(2-((3'-(5-(5-(tert-butoxy)-5-oxopentyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-2,2'-dichloro-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C
  • 24
  • [ 1350821-95-2 ]
  • 4-(2-(2-((2,2'-dichloro-3'-(5-(5-(dimethylamino)-5-oxopentyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 1 h / 40 °C 5.2: 2 h / 20 °C 5.3: 3 h / 30 °C
  • 25
  • [ 1350821-95-2 ]
  • methyl 4-(2-oxoethyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium-t-butoxide / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C
Multi-step reaction with 2 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium-t-butoxide / tetrahydrofuran / 1 h / 20 °C 2.2: 5 h / 20 °C 2.3: 1 h / 20 °C
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 20 °C 2.1: potassium-t-butoxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 2.2: 3 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride; water monomer / tetrahydrofuran / 2 h / 20 °C
  • 26
  • [ 1350821-95-2 ]
  • methyl 4-(2-(2-((2,2'-dichloro-3'-(1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C 2.2: 5 h / 20 °C 2.3: 1 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 3 h / 20 °C 3.2: 1 h / 20 °C
  • 27
  • [ 1350821-95-2 ]
  • 4,4'-(((((2,2'-dichloro-[1,1'-biphenyl]-3,3'-diyl)bis(azanediyl))bis(carbonyl))bis(1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-2,5-diyl))bis(ethane-2,1-diyl))bis(bicyclo[2.2.1]heptane-1-carboxylic acid) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C 2.2: 5 h / 20 °C 2.3: 1 h / 20 °C 3.1: toluene-4-sulfonic acid / 2 h / 50 °C 4.1: potassium hydroxide; water / tetrahydrofuran / 3.5 h / 40 °C 5.1: hydrogenchloride / tetrahydrofuran; water / 1.5 h / 20 °C 6.1: dichloromethane; isopropyl alcohol / 1.5 h 6.2: 2.5 h / 20 - 35 °C
  • 28
  • [ 1350821-95-2 ]
  • methyl 4-(2-(2-((2-chloro-2'-methyl-3'-(1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C
  • 29
  • [ 1350821-95-2 ]
  • methyl 4-(2-(2-((2'-chloro-2-methyl-3'-(1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C
  • 30
  • [ 1350821-95-2 ]
  • methyl 4-(2-(2-((2-chloro-2'-cyano-3'-(1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C
  • 31
  • [ 1350821-95-2 ]
  • 4-(2-(2-((2,2'-dimethyl-3'-(1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol / 3 h / 30 °C
  • 32
  • [ 1350821-95-2 ]
  • 4,4'-(((((2,2'-dimethyl-[1,1'-biphenyl]-3,3'-diyl)bis(azanediyl))bis(carbonyl))bis(1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-2,5-diyl))bis(ethane-2,1-diyl))bis(bicyclo[2.2.1]heptane-1-carboxylic acid) trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 3 h / 30 °C 3.3: pH 2
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 4.2: 3 h / 30 °C 4.3: pH 2
  • 33
  • [ 1350821-95-2 ]
  • (R)-4-(2-(2-((3'-(5-(2-hydroxypropyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-2,2'-dimethyl-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / 2 h / 20 °C 4.2: 2 h / 40 °C
  • 34
  • [ 1350821-95-2 ]
  • 4-(2-(2-((2,2’-dichloro-3’-(5-(4-hydroxycyclohexyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1’-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / 2 h / 20 °C 5.1: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol 5.2: pH 2
  • 35
  • [ 1350821-95-2 ]
  • 4-(2-(2-((3'-(5-(2-(trans-4-carboxycyclohexyl)ethyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-2,2'-dichloro-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 4.2: 3 h / 30 °C 4.3: pH 2
  • 36
  • [ 1350821-95-2 ]
  • 4-(2-(2-((3'-(5-(4-carboxybutyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-2,2'-dichloro-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 5.1: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 1 h / 40 °C 5.2: 3 h / 30 °C 5.3: pH 2
  • 37
  • [ 1350821-95-2 ]
  • 4-(2-(2-((3'-(5-(cis-4-carboxy-4-methylcyclohexyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-2,2'-dichloro-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 40 °C
  • 38
  • [ 1350821-95-2 ]
  • 4-(2-(2-((2-chloro-3’-(5-(4-hydroxycyclohexyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-2’-methyl-[1,1’-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 5.1: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol / 2 h / 30 °C 5.2: pH 2
  • 39
  • [ 1350821-95-2 ]
  • 4-(2-(2-((2,2'-dichloro-3'-(1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol / 3 h / 30 °C
  • 40
  • [ 1350821-95-2 ]
  • 4-(2-(2-((2,2'-dichloro-3'-(1-methyl-5-(tetrahydro-2H-pyran-4-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 4.2: 3 h / 30 °C 4.3: pH 2
  • 41
  • [ 1350821-95-2 ]
  • (R)-4-(2-(2-((2,2'-dichloro-3'-(5-(2-hydroxypropyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 4.2: 2 h / 40 °C
  • 42
  • [ 1350821-95-2 ]
  • 4,4'-(((((2,2'-dichloro-[1,1'-biphenyl]-3,3'-diyl)bis(azanediyl))bis(carbonyl))bis(1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-2,5-diyl))bis(ethane-2,1-diyl))bis(bicyclo[2.2.1]heptane-1-carboxylic acid) trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C 2.2: 5 h / 20 °C 2.3: 1 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 3 h / 30 °C 3.3: pH 8
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 20 °C 2.2: 5 h / 20 °C 2.3: 1 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 3 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 4.2: 3 h / 30 °C 4.3: pH 8

  • 43
  • [ 1350821-95-2 ]
  • 4-(2-(2-((2-chloro-2'-methyl-3'-(1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol / 3 h / 30 °C 4.2: pH 2
  • 44
  • [ 1350821-95-2 ]
  • 4-(2-(2-((2-chloro-2'-methyl-3'-(1-methyl-5-(tetrahydro-2H-pyran-4-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 4.2: 3 h / 30 °C 4.3: pH 2
  • 45
  • [ 1350821-95-2 ]
  • (R)-4-(2-(2-((2-chloro-3'-(5-(2-hydroxypropyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-2'-methyl-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 4.2: 2 h / 40 °C
  • 46
  • [ 1350821-95-2 ]
  • 4-(2-(2-((2'-chloro-2-methyl-3'-(1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)ethyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: lithium hydroxide monohydrate / tetrahydrofuran; water; methanol / 3 h / 30 °C 4.2: pH 2
  • 47
  • [ 1350821-95-2 ]
  • 4-((2-((3'-(5-(2-(4-carboxybicyclo[2.2.1]heptan-1-yl)ethyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-2-carboxamido)-2-chloro-2'-methyl-[1,1'-biphenyl]-3-yl)carbamoyl)-1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl)methyl)bicyclo[2.2.1]heptane-1-carboxylic acid trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 2.2: 3 h / 30 °C 2.3: pH 2
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 4.2: 3 h / 30 °C 4.3: pH 2
  • 48
  • [ 1350821-95-2 ]
  • 4,4'-(((((2-chloro-2'-cyano-[1,1'-biphenyl]-3,3'-diyl)bis(azanediyl))bis(carbonyl))bis(1-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-2,5-diyl))bis(ethane-2,1-diyl))bis(bicyclo[2.2.1]heptane-1-carboxylic acid) trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.3: pH 2
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 1 h / 250 °C 2.2: 5 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 3.2: 1 h / 20 °C 4.1: sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C 4.3: pH 2
  • 49
  • [ 1350821-95-2 ]
  • [ 7143-01-3 ]
  • C11H18O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0 - 25℃; for 2h; 85.2 Step 2: 143-3 To a mixture of crude 143-2 (450 mg, 2.44 mmol) , Triethylamine (741.49 mg, 7.33 mmol, 1.02 mL) in DCM (15 mL) was added Methanesulfonic anhydride (638.24 mg, 3.66 mmol) at 0 . The reaction solution was stirred for 2 hr at 25 . Then, the solution was concentrated with a rotary evaporator to obtain 143-3 (660 mg, crude) .
  • 50
  • [ 1350821-95-2 ]
  • [ 74-88-4 ]
  • C11H18O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.21% With silver(I) oxide In N,N-dimethyl-formamide at 20℃; for 16h; 8 I-8d2 (25.00g, 135.70mmol, 1.0eq) was dissolved in DMF (100mL), MeI (192.61g, 1.36mol, 10.0eq) and Ag2O (94.34g, 407.10mmol, 3.0eq) were added in one portion. After the addition, the reaction system had no obvious exothermic and gassing phenomena. The reaction was stirred at room temperature 20 °C overnight for 16 h. TLC showed the reaction was complete. The insolubles were removed by filtration, the filtrate was poured into 1 L of water, and extracted with EA (100 mL×3). The aqueous phase was discarded, and the organic phase was washed once with saturated brine (200 mL). The organic phase was dried over magnesium sulfate, filtered and spun dry. The crude product was separated by silica gel column chromatography (PE/EA (v/v)=30/1) to obtain a pale yellow liquid I-8d3 (24.00 g, yield 89.21%). 1H-NMR (400MHz, CDCl 3) δppm 3.66(s, 3H), 3.42(s, 2H), 3.35(s, 3H), 2.04(m, 2H), 1.94(m, 4H), 1.56(s, 2H) ),1.38(m,2H).
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