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Chemical Structure| 19230-71-8 Chemical Structure| 19230-71-8

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Chemical Structure| 19230-71-8

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Product Details of [ 19230-71-8 ]

CAS No. :19230-71-8
Formula : C3H5N3
M.W : 83.09
SMILES Code : CC1=NNN=C1
MDL No. :MFCD20482150
InChI Key :GVSNQMFKEPBIOY-UHFFFAOYSA-N
Pubchem ID :12933420

Safety of [ 19230-71-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 19230-71-8 ]

* 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 [ 19230-71-8 ]

[ 19230-71-8 ] Synthesis Path-Downstream   1~12

  • 1
  • C33H25N6O3P [ No CAS ]
  • [ 19230-71-8 ]
  • [ 81787-18-0 ]
  • 4
  • [ 19230-71-8 ]
  • (E)-(1-(3-(4-chloro-2-((5-methyl-2H-tetrazol-2-yl)methyl)phenyl)acryloyl)piperidin-4-yl)methyl methanesulfonate [ No CAS ]
  • (E)-3-(4-chloro-2-((5-methyl-2H-tetrazol-2-yl)methyl)phenyl)-1-(4-((4-methyl-2H-1,2,3-triazol-2-yl)methyl)piperidin-1-yl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
To 4-methyl-i H-i ,2,3-triazole (commercially available) (128 mg, 1.536 mmol) in DMF (5 mL) was added sodium hydride (60% in mineral oil) (66.5 mg, 1.664 mmol) and the resulting mixture was stirred for 5 minutes. (E)-(i -(3-(4-chloro-2-((5-methyl-2 H-tetrazol-2-yl)methyl)phenyl)acryloyl)piperidin-4-yl)methyl methanesulfonate (Example 109, step 2)(581 mg, 1.280 mmol) was added and the mixture was heated to 12000 for 3 h. The reaction mixture was left to cool and was poured into EtOAc and washed with excess water, brine and dried over a phase separator. The solvent was removed under reduced pressure. Purification of the crude product by chromatography on silica using a gradient from 0 - 100%EtOAc in iso-hexane followed by 10% methanol in EtOAc afforded the title compound; LCMS: Rt= 1.23mins; [M+H]441.5, Method 2minLowpHvo3.
  • 5
  • [ 19230-71-8 ]
  • [ 141699-59-4 ]
  • tert-butyl 4-(4-methyl-2H-1,2,3-triazol-2-yl)piperidine-1-carboxylate [ No CAS ]
  • tert-butyl 4-(4-methyl-1H-1,2,3-triazol-1-yl)-piperidine-1-carboxylate [ No CAS ]
  • tert-butyl 4-(5-methyl-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
4-Methyl-iH-i,2,3-triazole (357 mg, 4.30 mmol) was placed in a flask with dry DMF (5 mL). Sodium hydride (186 mg, 4.65 mmol) was added and the reaction mixture was stirred atroom temperature for 15 minutes. tert-Butyl 4-((methylsulfonyl)oxy)piperidine- 1 -carboxylate (step 1) (1.00 g, 3.58 mmol) was added and the reaction mixture was stirred at 100C for4 hours. The resulting mixture was partitioned between EtOAc and water. The organic phase was washed with water and brine, dried over Mg504, filtered and the solvent was removedvacuo. The product was purified by chromatography on silica eluting with iso-hexane/(EtOAc:MeOH - 10:1) to afford:Product Step 2a: tert- Butyl 4-(4-methyl-2 H- 1,2, 3-triazol-2-yl)piperidine- 1 -carboxylate;1H NMR (400 MHz, DMSO-d6) O 7.52 (iH, 5), 4.60 (iH, m), 3.93 (2H, m), 2.98 (2H, m), 2.21(3H, 5), 2.03 (2H, m), 1.80 (2H, m), 1.40 (9H, 5).Product Step 2b: tert- Butyl 4-(4-methyl- 1 H- 1,2, 3-triazol- 1 -yl)piperidine- 1 -carboxylate;1H NMR (400 MHz, DMSO-d6) O 7.91 (iH, 5), 4.62 (iH, m), 4.02 (2H, m), 2.92 (2H, m), 2.21(3H, 5), 2.01 (2H, m), 1.80 (2H, m), 1.42 (9H, 5).Product Step 2c: tert-Butyl 4-(5-methyl- 1 H- 1,2, 3-triazol- 1 -yl) piperidine- 1 -carboxylate;1H NMR (400 MHz, DMSO-d6) O 7.49 (1H, s), 4.51 (1H, m), 4.08 (2H, m), 2.97 (2H, m), 2.31(3H, s), 1.95 (2H, m), 1.87 (2H, m), 1.42 (9H, s).
  • 6
  • [ 19230-71-8 ]
  • [ 1430065-01-2 ]
  • C24H36FN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
20.83% With potassium carbonate; In N,N-dimethyl-formamide; at 28℃; for 2h; To a solution of SV (100mg, 0.24 mmol) in 15 mL of DMF was added 4-methyl-2H-1, 2, 3-triazole (40.01 mg, 0.48 mmol) and K2C03 (99.82 mg, 0.72 mmol). The reaction was stirred at 28C for 2 h. The resulting solution was quenched with water and extracted with EtOAc (50 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuum. The residue was purified byprep-HPLC to give SV-7 (20.6 mg, yield: 20.83%) as an off white solid. 111 NMR (SV-7): (400 MHz, CDC13) ö 7.45 (s, 1 H), 5.23-5.10 (m, 2H), 4.68-4.49 (m, 1H), 2.64-2.57 (m, 1H), 2.35 (s, 3H), 2.30-2.18 (m, 1H), 2.14-2.00 (m, 2H), 1.93-1.58 (m, 8H), 1.46-1.09 (m, 13H) , 0.86-0.76 (m, 1H), 0.75 (s , 3H).
  • 7
  • [ 19230-71-8 ]
  • [ 1430065-01-2 ]
  • C24H36FN3O2 [ No CAS ]
  • C24H36FN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
29.84%; 23.3% With potassium carbonate; In N,N-dimethyl-formamide; at 17℃; for 2h; To a solution of SV (200 mg, 0.48 mmol) in 10 mL of DMF (5 mL) was added <strong>[19230-71-8]4-methyl-2H-1,2,3-triazole</strong> (80.02 mg, 0.96 mmol) and K2C03 (199.63 mg, 1.44 mmol). The reaction mixture was stirred at 17C for 2 h. The resulting solution was quenched with water and extracted with EtOAc (50 mL). The organic layer was dried and concentrated. The residue was purified by silica gel to give a 90 mg mixture of SV-8/SV-9anda byproduct(60 mg). The mixture was split by SFC purification to give SV-8 (38.8 mg, yield: 29.84%) andSV-9(31.5 mg, yield: 23.3%) as off white solid.1H NMR (SV-8): (400 MHz, CDC13) ö 7.347 (s, 1 H), 5.191-5.041 (q,J117.6 HMz,J242.4 HMz), 4.62-4.50 (m, 1H), 2.66-2.61 (m, 1H), 2.37 (s, 3H), 2.10-2.06 (m, 1H), 1.87-1.74 (m, 2H), 1.70-1.50 (m, 7H), 1.30-1.04 (m, 14H) , 0.86-0.76 (m, 1H), 0.70 (s , 3H).1H NMR (SV-9): (400 MHz, CDC13) ö 7.488 (s, 1 H), 5.08-5.07 (m, 2H), 4.63-4.50 (m, 1H), 2.68-2.63 (m,1H), 2.22 (s, 3H), 2.04-1.89 (m, 2H), 1.80-1.73 (m, 7H), 1.64-1.60 (m, 1H), 1.56-1.20 (m, 14H) , 0.80-0.70 (m, 1H), 0.64 (s , 3H).
  • 8
  • [ 19230-71-8 ]
  • [ 1430063-93-6 ]
  • 3α-hydroxy-3β-methyl-21-(4-methyl-2H-1,2,3-triazol-2'-yl)-19-nor-5β-pregnan-20-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
26.59% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h; To a suspension of SA (1 g, 2.52 mmol) in DMF (20 mL) was added K2C03 (1.04 g, 7.55 mmol) and 4-methyl-2H- 1,2,3 -triazole (313.64 mg, 3.77 mmol). The mixture was stirred at room temperature for 3h. Then the reaction mixture was poured into S mL H20 and extracted with EtOAc (30 mL). The combined organic layers were washed with brine (10 mL*3), dried over sodium sulfate, filtered and concentrated. The residue was purified with by prep-HPLC to afford the title compound SA-3 (269.2 mg, Yield=26.59%) as an off white solid.1HNMR(SA-3) (400 MHz, CDC13) 67.42 (s, 1H), 5.14-5.13 (m, 2H), 2.57-2.56 (m, 1H),2.33 (s, 3H), 2.01-2.00 (m, 2H), 1.81-1.70 (m, 6H), 1.45-1.39 (m, 7H), 1.27-1.24 (m, 9H), 1.01-1.00 (m,3H), 0.70 (s , 3H).
  • 9
  • [ 19230-71-8 ]
  • [ 1430063-93-6 ]
  • 3α-hydroxy-3β-methyl-21-(5-methyl-1H-1,2,3-triazol-1'-yl)-19-nor-5β-pregnan-20-one [ No CAS ]
  • 3α-hydroxy-3β-methyl-21-(4-methyl-1H-1,2,3-triazol-1'-yl)-19-nor-5β-pregnan-20-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
12.5%; 21.3% With potassium carbonate; In N,N-dimethyl-formamide; at 13 - 17℃; for 4h;Inert atmosphere; To a solution of <strong>[19230-71-8]4-methyl-2H-1,2,3-triazole</strong> (836.4 mg, 10.07 mmol) and K2C03 (1.39 g, 10.07 mmol) in DMF (20 mL)was added compoundSA (2.0 g, 5.03 mmol) at room temperature (13-17C)underN2. The reaction mixture was stirred at room temperature (13-17 C) for 4 h. TLC showed the reaction was completed. Then the reaction mixture was poured into water and extracted with EtOAc (50 mLx3). Thecombined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel to afford730 mg mixture of SA-4/SA-Sand a byproduct (500 mg, yield :25%). The mixture was split by SFC purification to give SA-4 (249.8 mg, yield: 12.5%) andSA-5(426.2 mg, yield:21.3%) as off white solid.1H NMR (SA-4): (400 MHz, CDC13) ö 7.49 (s, 1H), 5.14-5.02 (m, 2H), 2.67-2.63 (m, 1H), 2.21-2.16 (m, 4H), 2.11-2.08 (m, 1H), 1.88-1.75 (m, 6H), 1.65-1.55(m, 1H), 1.5 1-1.37 (m, 7H), 1.33-1.22 (m, 8H), 1.14-1.08 (m, 3H), 0.69 (s, 3H).1H NMR (SA-5): (400 MHz, CDC13) ö 7.35 (s, 1H), 5.20-5.04 (m, 2H), 2.65-2.61 (m, 1H), 2.38 (s, 3H), 2.25-2.17 (m, 1H), 2.09- 2.05 (m, 1H), 1.88-1.63 (m, 7H), 1.50-1.28 (m, 15H), 1.15-1.06 (m, 3H), 0.67 (s, 3H).
  • 10
  • [ 203786-30-5 ]
  • [ 19230-71-8 ]
  • C26H41N3O3 [ No CAS ]
  • C26H41N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetone; at 25℃; for 12h; General procedure: Step 8. Symthesis of 139. K2CO3 (125 mg, 906 umol) was added to a solution of A55 (200 mg, 453 umol) and 4-methyl-1H-pyrazole (48 mg, 588 umol) in acetone (3 mL) at 25C. The resulting mixture was stirred at 25 C for 12 hours, at which point TLC indicated the reaction was complete. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (10 mL*3).The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered, and evaporated to afford crude product (200 mg). The reaction mixture was purified by HPLC (column: Waters Xbridge Prep OBD C18150*305u, gradient: 44-74% B (A=0.05%ammonia-ACN, B=acetonitrile), flow rate: 25 mL/min) to obtain Compound 139 (53.6 mg) as a white solid. 1HNMR (Chloroform-d, 400 MHz) δ = 7.34 (s, 1H), 7.17 (s, 1H), 4.77- 4.91 (m, 2H), 3.39 (s, 3H), 3.18 (s, 2H), 2.57 (t, J=8.8 Hz, 1H), 2.14-2.23 (m, 1H), 2.09 (s, 3H), 1.98-2.06 (m, 2H), 1.63-1.74 (m, 4H), 1.50-1.55 (m, 2H), 1.10-1.50 (m, 12H), 0.94-1.02 (m, 1H), 0.80-0.87 (m, 1H), 0.75 (s, 3H), 0.67 ppm (s, 3H). LCMS Rt = 2.848 min in 4 min chromatography, MS ESI calcd. for C27H42N2O3 [M+Na]+ 465.3, found 465.1 ([M+H-18]+). The title compounds were prepared according to Example 67. Compound 183: 1H NMR (CDCl3, 400MHz): δ7.35 (s, 1H), 5.03-5.21 (m, 2H), 3.39 (s, 3H), 3.19 (s, 2H), 2.63 (t, J=8.8 Hz, 1H), 2.38 (s, 3H), 2.15-2.25 (m, 1H), 1.99-2.10 (m, 2H), 1.63- 1.77 (m, 4H), 1.10-1.58 (m, 14H), 0.95-1.04 (m, 1H), 0.81-0.89 (m, 1H), 0.76 (s, 3H), 0.66 (s, 3H). LCMS Rt = 2.657 min in 4 min chromatography, MS ESI calcd. for C26H41N3O3 [M+H]+ 444.3, found 444.1 ([M+H]+. Compound 184: 1H NMR (DMSO-d6, 400MHz): δ7.49 (s, 1H), 5.46 (d, J=18.6 Hz, 1H), 5.23 (d, J=18.6 Hz, 1H), 4.02 (s, 1H), 3.24 (s, 3H), 3.04 (s, 2H), 2.80 (t, J=9.0 Hz, 1h), 2.67 (br. s., 1H), 2.33 (br. s., 1H), 2.13 (s, 3H), 2.04 (d, J=8.0 Hz, 1H), 1.64 (d, J=16.6 Hz, 4H), 1.49 (d, J=9.0 Hz, 13H), 0.93 (d, J=9.6 Hz, 1H), 0.76 (d, J=9.6 Hz, 1H), 0.70 (s, 3H), 0.58 (s, 3H). LCMS Rt = 2.683 min in 4 min chromatography, MS ESI calcd. for C26H41N3O3 [M+H]+ 444.3, found 444.1 ([M+H]+.
  • 11
  • [ 19230-71-8 ]
  • 2-bromo-1-((3R,5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-3,10,13-trimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone [ No CAS ]
  • C25H39N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 30℃; General procedure: Step 4. Synthesis of A21 and A22. To a solution of A20 (1.4 g, 3.28 mmol) and 2H-1,2,3- triazole (1.13 g, 16.41 mmol) in DMF (25 mL) was added K2CO3 (2.27 g, 16.41 mmol). The reaction was stirred at 30 oC overnight. TLC (petroleum ether/ethyl acetate=1/2) showed that the reaction was completed. The reaction was added brine (20 mL). The resulting solution was extracted with EtOAc (25 mL*3). The combined organic layers was dried and concentrated to give crude, which was purified by column chromatagraphy on silica gel (ethyl acetate/petroleum ether=2/1 to 1/2) to afford A21 (460 mg) and A22 (480 mg) as white solid. Example 8. Synthesis of 13. The title compounds were prepared according to Example 5, step 4. 1H NMR (13): (400 MHz, CDCl3) δ 7.41 (s, 1H), 5.13-5.12 (m, 2H), 2.57-2.52 (m, 1H), 2.32 (s, 3H), 2.25-2.15 (m, 1H), 2.10-2.00 (m, 1H), 1.94-1.59 (m, 5H), 1.52-1.40 (m, 9H), 1.26-1.06 (m, 10H), 0.94 (s, 3H), 0.67 (s, 3H). LCMS Rt = 0.93 min in 1.5 min chromatography, 5-95AB, MS ESI calcd. For C25H40N3O2 [M+H]+ 414, found 414.
  • 12
  • [ 19230-71-8 ]
  • [ 66192-24-3 ]
  • C10H9BrClN3 [ No CAS ]
 

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