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Chemical Structure| 479234-83-8
Chemical Structure| 479234-83-8
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Product Details of [ 479234-83-8 ]

CAS No. :479234-83-8 MDL No. :MFCD12911715
Formula : C11H12N4 Boiling Point : -
Linear Structure Formula :- InChI Key :YAHHFPJGDOWLGU-UHFFFAOYSA-N
M.W : 200.24 Pubchem ID :135741977
Synonyms :

Safety of [ 479234-83-8 ]

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 [ 479234-83-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 479234-83-8 ]

[ 479234-83-8 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 31037-02-2 ]
  • [ 479234-83-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 62 percent / NaH / tetrahydrofuran 2: 92 percent / H2 / Pd/C / methanol 3: 40 percent / dimethylsulfoxide / 2.5 h / 75 °C 4: 98 percent / LiAlH4 / tetrahydrofuran
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 48 h 2: acetic acid / isopropyl alcohol / 48 h / 160 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 44 h / Reflux
  • 2
  • [ 1975-53-7 ]
  • [ 479234-83-8 ]
  • [ 744200-39-3 ]
YieldReaction ConditionsOperation in experiment
87% Thionyl chloride (0.8 ml, 11.00 mmol) was added to a suspension of <strong>[1975-53-7]4-Cyano-2-methylbenzoic acid</strong> (630 mg, 3.91 mmol) in toluene (30 ml). The mixture was heated at reflux for 2h, allowed to cool and concentrated in vacuo. The residue was azeotroped with toluene and then taken up in dichloromethane (25ml). The resulting solution was added to a stirred solution of 1-methyl-4,10-dihydropyrazolo[5,4-b][1,5]benzodiazepine (706 mg, 3.53 mmol) and triethylamine (0.70ml, 5.02mmol) in dichloromethane (25ml). The mixture was heated at reflux for 18h and cooled. The mixture was diluted with dichloromethane and washed with 0.3 M KHSO4, saturated NaHCO3 and brine then concentratedin vacuo. The residue was purified by flash chromatography on silica gel (eluant ethyl acetate) to give an off-white solid identified as 3-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-benzonitrile (1.06 g, 87%).
  • 3
  • [ 73831-13-7 ]
  • [ 479234-83-8 ]
  • [ 479234-62-3 ]
YieldReaction ConditionsOperation in experiment
87% Thionyl chloride (1.8 ml, 27 mmol) was added to a stirred suspension of <strong>[73831-13-7]4-cyano-3-methylbenzoic acid</strong> (1.29 g, 8.0 mmol) in toluene (25 ml). The mixture was heated at reflux for 2 h, cooled to room temperature and concentratedin vacuo. The residue was azeotroped with toluene then dissolved in dichloromethane (10 ml). The resulting solution was added to a stirred suspension of 1-methyl-4,10-dihydropyrazolo[5,4-b][1,5]benzodiazepine (1.6 g, 8 mmol) and triethylamine (1.4 ml, 10 mmol) in dichloromethane (15 ml). The mixture was stirred overnight at room temperature then concentrated in vacuo. The residue was partitioned between chloroform and 0.3M KHSO4. The aqueous phase was extracted with chloroform/2-propanol (80:20). The combined organic phases were washed with sat. NaHCO3 and brine, dried over Na2SO4 and concentratedin vacuo. The residue was purified by flash chromatography on silica gel (eluant 5% methanol/chloroform) to give a pale yellow solid identified as 5-(4-cyano-3-methylbenzoyl)-1-methyl-4,10-dihydropyrazolo[5,4-b][1,5]-benzodiazepine (2.4 g, 87%).
  • 4
  • [ 117007-77-9 ]
  • [ 479234-83-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide / 2 h / 120 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 16 h / 20 °C / 760.05 Torr / Inert atmosphere
Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide / 100 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr
Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide / 2 h / 120 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / methanol / 16 h / 20 °C / 760.05 Torr
  • 5
  • [ 828-51-3 ]
  • [ 479234-83-8 ]
  • ((3r,5r,7r)-adamantan-1-yl)(1-methyl-4,10-dihydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; Cooling with ice; 19 General procedure: An ice cold magnetically stirred solution of the required benzoic acid (1 .1 mmol), amine 1 (200 mg, 1 mmol) and 'Pr2NEt (348 μΙ_, 2 mmol) in CH2CI2 (20 mL) was treated with PyBOP (500 mg, 1 mmol) in portions, allowed to warm to room temperature and stirring continued for 4 h. The reaction mass was diluted with CH2CI2 (50 mL) and water (50 mL), the separated organic phase was subsequently washed with NaHCO3 (25 mL of a sat. aq. solution) and brine (100 mL) before being dried (MgSO4), filtered and purified via flash column chromatography (silica, 1 :1 to 1 :0 v/v EtOAc/hexanes gradient elution) produced the required amides as crystalline solids.
  • 6
  • [ 129714-97-2 ]
  • [ 479234-83-8 ]
  • (3,5-difluorophenyl)(1-methyl-4,10-dihydrobenzo[b]pyrazolo[3,4- e][1,4]diazepin-5(1H)-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With triethylamine In dichloromethane at 0 - 20℃; for 4h; 3 General procedure: A magnetically stirred suspension of 1 (200 mg, 1 mmol) and NEt3 (229 μ, 2 mmol) in CH2CI2 (10 mL) was treated with a solution of the appropriate benzoyl chlorides (1 .1 mmol) in CH2CI2 (10 mL) dropwise at 0 °C. The reaction mixture was then warmed to room temperature and stirring continued for 4 h. The resultant solution was diluted with CH2CI2 (25 mL) and NaHCO3 (25 mL of a sat. aq. solution), the separated organic phase was subsequently washed with NaHCO3 (25 mL of a sat. aq. solution) and brine (50 mL) before being dried (MgSO4), filtered and concentrated under reduced pressure to give crude oils (of compounds of the Formula 1 a). Purification by either trituration (EtOAc) followed by recrystallisation (MeOH/CH2Cl2) or via flash chromatography afforded the required amides
  • 7
  • [ 29654-55-5 ]
  • [ 479234-83-8 ]
  • 5-((1-methyl-4,10-dihydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)methyl)benzene-1,3-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With sodium tris(acetoxy)borohydride In dichloromethane for 12h; 64 5-((1-methyl-4,10-dihydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)methyl)benzene-1,3-diol(WJ0627) A stirred solution of diazepine 1 (150 mg, 0.75 mmol) and resorcinal (104 mg, 0.75 mmol) in CH2CI2 (10 mL) was treated portion wise with sodium triacetoxyborohydride (795 mg, 3.75 mmol) over 1 h and stirring continued for 12 h. The resultant suspension was diluted with CH2CI2 (25 mL) and subsequently washed with NaHCO3 (25 mL of a sat. aq. solution), brine (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure followed by purification via flash column chromatography (silica, 2.5:97.5 v/v MeOH:CH2CI2) produced the title compound (1 1 1 mg, 46%) as a white crystalline powder (R, = 0.04 in a 2.5:97.5 v/v MeOH:CH2CI2 solution).1H NMR (400 MHz, DMSO-afe): 9.09 (br d, J = 2.2 Hz, 2H, 20 H), 8.08 (br s, 1 H, NH), 7.16 (dd, J = 8.0, 1 .5 Hz, 1 H, 3-CH), 7.05 (dd, J = 8.0, 1 .5 Hz, 1 H, 6-CH), 6.95 (td, J = 7.6, 1 .5 Hz, 1 H, 2-CH), 6.90 (s, 1 H, 12-CH), 6.81 (td, J = 7.5, 1 .5 Hz, 1 H, 1 -CH), 6.20 (d, J = 2.1 Hz, 2H, 16-2xCH), 6.05 (t, J = 2.2 Hz, 1 H, 18-CH), 3.93 (s, 2H, 10-CH2), 3.76 (s, 2H, 8-CH2), 3.72 (s, 3H, 15-CH3). 13C NMR (101 MHz, DMSO-afe): δ 158.2, 141 .5, 141 .4, 140.5, 138.8, 135.7, 125.0, 124.1 , 121 .1 , 1 19.5, 106.2, 101 .2, 100.4, 57.9, 48.8, 35.1 . IR (diamond cell, neat) vmax: 3334, 1586, 1553, 1499, 1440, 1386, 1297, 1213, 1 157, 1002, 956, 833, 762, 744, 688, 619, 559, 529, 439 cm-1. LRMS (+ ESI) m/z: 323 [(M+H) 1 00%]. HRMS (+ ESI) Found: (M+H) 323.1 503. C18H18N4O2 requires (M+H) 323.1503. MP 236-238 °C. HPLC purity: 95.51 %, RT: 13.01 min.
  • 8
  • [ 73391-96-5 ]
  • [ 479234-83-8 ]
  • N-benzyl-N-methyl-2-(1-methyl-4,10-dihydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine In tetrahydrofuran at 20℃; for 19h; Inert atmosphere; 6.1. General procedure for the synthesis of 5a-5d General procedure: To a solution of 16 (100 mg, 0.499 mmol, 1.0 equiv.) in tetrahydrofuran(1 mL) was added triethylamine (140 μL, 0.999 mmol, 2.0equiv.), followed by the dropwise addition of the appropriatealkylating agent (1.1 equiv.). The reaction mixture was stirred atambient temperature for 19 h. The reaction mixture was evaporatedto dryness and diluted with ethyl acetate (5 mL) and water(2 mL). The organic layer was collected, and the aqueous layer wasfurther extracted with ethyl acetate (2 x 5 mL). The combinedorganic extracts werewashed with aqueous hydrochloric acid (1 M,2 mL), followed by water (2 mL). The organic layer was dried overmagnesium sulfate and concentrated in vacuo. Purification by flashchromatography on silica gel column using methanol/dichloromethane(5:95 v/v) furnished the desired pyrazolobenzodiazepine ligands.
  • 9
  • [ 2315-36-8 ]
  • [ 479234-83-8 ]
  • N,N-diethyl-2-(1-methyl-4,10-dihydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With triethylamine In tetrahydrofuran at 20℃; for 19h; Inert atmosphere; 6.1. General procedure for the synthesis of 5a-5d General procedure: To a solution of 16 (100 mg, 0.499 mmol, 1.0 equiv.) in tetrahydrofuran(1 mL) was added triethylamine (140 μL, 0.999 mmol, 2.0equiv.), followed by the dropwise addition of the appropriatealkylating agent (1.1 equiv.). The reaction mixture was stirred atambient temperature for 19 h. The reaction mixture was evaporatedto dryness and diluted with ethyl acetate (5 mL) and water(2 mL). The organic layer was collected, and the aqueous layer wasfurther extracted with ethyl acetate (2 x 5 mL). The combinedorganic extracts werewashed with aqueous hydrochloric acid (1 M,2 mL), followed by water (2 mL). The organic layer was dried overmagnesium sulfate and concentrated in vacuo. Purification by flashchromatography on silica gel column using methanol/dichloromethane(5:95 v/v) furnished the desired pyrazolobenzodiazepine ligands.
  • 10
  • [ 1562-00-1 ]
  • [ 479234-83-8 ]
  • C11H12N4*C2H6O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol at 20 - 40℃; for 72h; 2 Example 2 - primary salt screen General procedure: A salt screen was conducted on 1-methyl-1 ,4,5,10-tetrahydropyrazolo[3,4- b][1 ,5]benzodiazepine freebase using 5 solvent systems and 18 acid counterions (see Table 1). (0228) The solvent systems used in this salt screen were (1) ethanol (EtOH); (2) tetrahydrofuran (THF); (3) isopropyl acetate; (4) acetone; and (5) 95% 2-propanol, 5% water (% v/v). The following procedure was used: Approximately 30 mg of 1 -methyl- 1 ,4, 5, 10-tetrahydropyrazolo[3, 4- b][1 ,5]benzodiazepine freebase was weighed into 5 x 1.5 mL glass vials. (0231) • 300 pL of selected solvent system was added to each vial to form a mobile slurry, and a beige slurry was observed. 1.05 (or 0.525 for the hemi experiments) equivalents of acid counterion (see Table 1) was added to each sample and initial observations were recorded. • The samples were temperature cycled between ambient and 40°C in 4-hour cycles for about 72 hours. The samples were collected, and observations made. Samples in which solids were observed were filtered via centrifugation and the solids were loaded onto a multi-well XRPD plate and analyzed by XRPD. Samples in which no solids were observed were uncapped and left undisturbed to allow evaporation at ambient temperature. Brown gums were observed in all samples postevaporation. The XRPD plate was placed in an oven at 40°C for about 24 hours. The dried samples analyzed by XRPD to identify any changes in pattern/ potential anhydrous salts. The XRPD plate was then placed in a stability chamber at 40°C/ 75% RH for about 24 hours. The post-stability samples were analyzed by XRPD to identify potential hydrate formation and disproportionation of salts. Observed patterns which were found to be stable upon drying and storage on 40°C/75% RH were analyzed by TG/DTA to identify salt forms suitable for scale up. During the primary salt screen of the 18 acid counterions tested, 16 produced potential solid salt forms of the compound. However, only the phosphate and L-tartrate salts possessed suitable properties based on thermal analysis and stability of the observed patterns at 40°C/ 75% RH.
  • 11
  • [ 1562-00-1 ]
  • [ 479234-83-8 ]
  • C11H12N4*0.5C2H6O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol at 20 - 40℃; for 72h; 2 Example 2 - primary salt screen A salt screen was conducted on 1-methyl-1 ,4,5,10-tetrahydropyrazolo[3,4- b][1 ,5]benzodiazepine freebase using 5 solvent systems and 18 acid counterions (see Table 1). (0228) The solvent systems used in this salt screen were (1) ethanol (EtOH); (2) tetrahydrofuran (THF); (3) isopropyl acetate; (4) acetone; and (5) 95% 2-propanol, 5% water (% v/v). The following procedure was used: Approximately 30 mg of 1 -methyl- 1 ,4, 5, 10-tetrahydropyrazolo[3, 4- b][1 ,5]benzodiazepine freebase was weighed into 5 x 1.5 mL glass vials. (0231) • 300 pL of selected solvent system was added to each vial to form a mobile slurry, and a beige slurry was observed. 1.05 (or 0.525 for the hemi experiments) equivalents of acid counterion (see Table 1) was added to each sample and initial observations were recorded. • The samples were temperature cycled between ambient and 40°C in 4-hour cycles for about 72 hours. The samples were collected, and observations made. Samples in which solids were observed were filtered via centrifugation and the solids were loaded onto a multi-well XRPD plate and analyzed by XRPD. Samples in which no solids were observed were uncapped and left undisturbed to allow evaporation at ambient temperature. Brown gums were observed in all samples postevaporation. The XRPD plate was placed in an oven at 40°C for about 24 hours. The dried samples analyzed by XRPD to identify any changes in pattern/ potential anhydrous salts. The XRPD plate was then placed in a stability chamber at 40°C/ 75% RH for about 24 hours. The post-stability samples were analyzed by XRPD to identify potential hydrate formation and disproportionation of salts. Observed patterns which were found to be stable upon drying and storage on 40°C/75% RH were analyzed by TG/DTA to identify salt forms suitable for scale up. During the primary salt screen of the 18 acid counterions tested, 16 produced potential solid salt forms of the compound. However, only the phosphate and L-tartrate salts possessed suitable properties based on thermal analysis and stability of the observed patterns at 40°C/ 75% RH.
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