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Product Details of [ 1269026-22-3 ]

CAS No. :1269026-22-3 MDL No. :MFCD29905280
Formula : C8H9BrN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :POYHGPKBZHOUBJ-UHFFFAOYSA-N
M.W : 261.07 Pubchem ID :88548109
Synonyms :

Safety of [ 1269026-22-3 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P270-P280-P301+P312+P330-P305+P351+P338-P337+P313-P501 UN#:
Hazard Statements:H302-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1269026-22-3 ]

* 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 [ 1269026-22-3 ]

[ 1269026-22-3 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 1269026-22-3 ]
  • [ 100-39-0 ]
  • [ 1269028-02-5 ]
YieldReaction ConditionsOperation in experiment
78% In toluene at 20℃; for 8h; 214 Reference Example 214 Production of ethyl 3-(benzyloxy)-6-bromo-5-methylpyrazine-2-carboxylate To a solution of the compound of Reference Example 111 (1.23 g, 4.71 mmol) in toluene (20 mL) were added silver carbonate (1.80 g, 6.53 mmol) and benzyl bromide (672 μL, 5.65 mmol) at 0°C, and the mixture was stirred at room temperature for 8 hr. The insoluble material was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=99:1→4:1) to give the title compound (1.29 g, 78%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ:1.28 (3 H, t, J=7.1 Hz), 2.60 (3 H, s), 4.33 (2 H, q, J=7.1 Hz), 5.46 (2 H, s), 7.29 - 7.46 (3 H, m), 7.46 - 7.55 (2 H, m).
  • 2
  • [ 609-09-6 ]
  • [ 1269026-22-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 21.5 h / 0 - 85 °C 2: NBS / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: ethanol / 20 h / 0 - 95 °C 2: NBS / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: ethanol / 1 h / 0 - 20 °C 2: NBS / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: ethanol / 0 °C / Reflux 2: NBS / N,N-dimethyl-formamide / 0 - 20 °C
Multi-step reaction with 2 steps 2: NBS
Multi-step reaction with 2 steps 1: ethanol / 0 - 20 °C / Reflux 2: NBS / N,N-dimethyl-formamide / 0 - 20 °C

  • 3
  • [ 141872-22-2 ]
  • [ 1269026-22-3 ]
YieldReaction ConditionsOperation in experiment
88% With NBS In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere; 207.2 Step 2. Synthesis of ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate A 500 mL flask was charged with ethyl 3-hydroxy-5-methylpyrazine-2-carboxylate (3 g, 16.4 mmol, 1 equiv) and DMF (65.6 mL) under a nitrogen atmosphere, and the resulting solution was cooled to 0 °C, followed by addition of BS (3.06 g, 17.2 mmol, 1.05 equiv). The resulting mixture was allowed to stir for 1 hour at room temperature, then diluted with water (150 mL) and ethyl acetate (200 mL). The layers were separated, and the resulting organic solution was then washed with water (150 mL), 1/2 saturated brine (2 x 150 mL), and brine (2 x 150 mL) sequentially. The organic solution was then dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2- carboxylate (3.77 g, 14.4 mmol, 88.0%) as a pale yellow solid. 1H NMR (500 MHz, DMSO-i) δ 4.30 (q, J= 7.1 Hz, 2H), 2.49 - 2.41 (br s, 3H), 1.29 (t, J= 7.1 Hz, 3H).
72% With NBS In N,N-dimethyl-formamide at 20℃; for 2.5h; Cooling with ice; Inert atmosphere; 1.2 Step 2: Preparation of ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate Ethyl 3-hydroxy-5-methylpyrazine-2-carboxylate (5.3 g, 29.09 mmol) was dissolved in 100 mL of DMF, and the solution was cooled in an ice water bath. NBS (5.4 g, 30.56 mmol) was added, and the reaction solution was stirred for 30 minutes. The reaction solution was warmed up to room temperature and stirred for for 2 hours. Water was added, and the solution was extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to obtain the product ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate (5.5 g, yield: 72%).MS m/z (ESI): 261.0 [M+H]+, 262.9 [M+2+H]+.
59% With NBS In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere; b Ethyl 6-(2.,3-dichlorophenvP-5-methyl-3-(tosyloxy)pyrazine-2-carboxylate, Intermediate AB Step b: To the stirred solution of ethyl 3-hydroxy-5-methylpyrazine-2-carboxylate (2.24 g, 12.3 mmol, 1.00 eq ) in DMF (11.2 mL) was added NBS (2.30 g, 12.9 mmol, 1.05 eq ) in one portion at 0 °C under N2, then the mixture was stirred at 20 °C for 2 h. The reaction mixture was poured into H20 (60.0 mL) where solid precipitate formed. The suspension was filtered and the solid filtrate was dried under reduced pressure to give ethyl 6-bromo-3 -hydroxy-5 - methylpyrazine-2-carboxylate (1.90 g, 59% yield) as a light yellow solid. LCMS m/z [M+H]+ = 262.9; 1H NMR (400MHz DMSO-r) 12.8 (br s, 1 H), 4.30 (q, J = 7.2 Hz, 2 H), 2.45 (s, 3 H), 1.29 (t, j= 7.2 Hz, 3 H).
14% With NBS In N,N-dimethyl-formamide at 0 - 20℃; 111 Reference Example 111 Production of ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate To a solution of the compound of Reference Example 110 (1.01 g, 5.54 mmol) in DMF (10 mL) was added N-bromosuccinimide (1.03 g, 5.79 mmol) at 0°C, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water (30 mL), and the mixture was extracted with ethyl acetate (30 mLx4). The extract was washed with brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitate was collected by filtration to give the title compound (1.04 g, 72%) as a white powder. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=99:1→4:1) to give the title compound (201 mg, 14%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ:1.29 (3 H, t, J = 7.1 Hz), 2.45 (3 H, s), 4.30 (2 H, q, J = 7.1 Hz), 12.80 (1 H, br s).
With NBS In dichloromethane at 0 - 25℃; for 0.166667h; Inert atmosphere; 6.2 [00706] To a solution of ethyl 3-hydroxy-5-methyl-pyrazine-2-carboxylate (166 g, 911.21 mmol) in DCM (1500 mL) was added NBS (178.40 g, 1.00 mol) in one portion at 0 °C under N2. The mixture was stirred at 25 °C for 10 min. The resulting mixture was diluted with saturated aq.Na2S03 (1000 mL) and the aqueous phase was extracted with DCM. The combined organic phase was washed with brine (50 mL), dried with anhydrous Na2S04, and concentrated under reduced pressure to afford ethyl 6-bromo-3-hydroxy-5-methyl-pyrazine- 2-carboxylate (230 g, crude) as a dark brown solid. MR (400 MHz, CDC13-d) δ ppm 4.54 (q, J=7.13 Hz, 2 H) 2.77 (s, 1H) 2.68 (s, 3 H) 1.46 (t, J=7.09 Hz, 3 H)
7.75 g With NBS In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere; 1 To a 0 solution of compound 1-1 (27.12 g, crude) in DMF (100 mL) under nitrogen atmosphere was added NBS (21.30 g, 0.12 mol) . The resulting mixture was allowed to warm to RT and stirred for 2 h. The reaction mixture was diluted with brine (100 mL) and EA (400 mL) . The organic layer was separated, washed with water (2 × 100 mL) and brine (3 × 100 mL) , dried over anhydrous Na 2SO 4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting with MeOH : DCM = 1 : 100, v/v) to give compound 1-2 (7.75 g) as a yellow solid. MS: 261 [M+1] +. 1HNMR (400 MHz, DMSO -d 6) δ 12.72 (brs, 1H) , 4.29 (q, J = 7.1Hz, 2H) , 2.44 (s, 3H) , 1.28 (t, J = 7.1Hz, 1H)
With NBS 1.2 Step 2: Step 2: ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate Ethyl 3-hydroxy-5-methylpyrazine-2-carboxylate (8.0g) was dissolved into N,N-dimethylformamide (60mL), and cooled to 0 °C. NBS (7.86g) was added into the solution, and the reaction was at room temperature overnight. Ice water (50mL) was added into the reaction solution and extracted by dichloromethane (50mL) for 3 times. Organic phase was washed with water (100mL), and dried by anhydrous sodium sulfate. Crude product was obtained after removal of solvent. The final product was obtained (7.2g) after purification with column chromatography (dichloromethane/methanol=100/1). LC-MS, (ES, m/z): [M+H]+ = 261.
7.2g With NBS In N,N-dimethyl-formamide at 0 - 20℃; 1.2 Step 2: ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate Ethyl 3-hydroxy-5-methylpyrazine-2-carboxylate (8.0g) was dissolved into N,N-dimethylformamide (60mL), and cooled to 0 °C. NBS (7.86g) was added into the solution, and the reaction was at room temperature overnight. Ice water (50mL) was added into the reaction solution and extracted by dichloromethane (50mL) for 3 times. Organic phase was washed with water (100mL), and dried by anhydrous sodium sulfate. Crude product was obtained after removal of solvent. The final product was obtained (7.2g) after purification with column chromatography (dichloromethane/methanol=100/1). LC-MS, (ES, m/z): [M+H]+ = 261.
7.2g With NBS In N,N-dimethyl-formamide at 0 - 20℃; 1.2 Step 2: ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate Ethyl 3-hydroxy-5-methylpyrazine-2-carboxylate (8.0g) was dissolved into N,N-dimethylformamide (60mL), and cooled to 0 °C. NBS (7.86g) was added into the solution, and the reaction was at room temperature overnight. Ice water (50mL) was added into the reaction solution and extracted by dichloromethane (50mL) for 3 times. Organic phase was washed with water (100mL), and dried by anhydrous sodium sulfate. Crude product was obtained after removal of solvent. The final product was obtained (7.2g) after purification with column chromatography (dichloromethane/methanol=100/1). LC-MS, (ES, m/z): [M+H]+ = 261.

  • 4
  • [ 1269026-22-3 ]
  • [ 98-80-6 ]
  • [ 1269026-24-5 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In ethanol; toluene at 80℃; for 1h; Inert atmosphere; 112 Reference Example 112 Production of ethyl 3-hydroxy-5-methyl-6-phenylpyrazine-2-carboxylate To a mixture of the compound of Reference Example 111 (1.20 g, 4.60 mmol), phenylboronic acid (835 mg, 6.84 mmol), toluene (30 mL) and ethanol (40 mL) were added potassium carbonate (3.15 g, 22.8 mmol) and Pd(PPh3)4 (268 mg, 0.232 mmol), and the mixture was stirred at 80°C for 1 hr under an argon atmosphere. Ethanol was evaporated under reduced pressure, and to the residue was added aqueous ammonium chloride solution (50 mL). The mixture was filtered through celite, and the organic layer was washed with brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=19:1→1:2) to give the title compound (1.10 g, 93%) as a yellow powder. 1H NMR (300 MHz, DMSO-d6) δ:1.28 (3 H, t, J = 7.2 Hz), 2.34 (3 H, s), 4.29 (2 H, q, J = 7.2 Hz), 7.27 - 7.59 (5 H, m), 12.88 (1 H, br s).
  • 5
  • [ 1269026-22-3 ]
  • ethyl 6-bromo-3-chloro-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.2% With N-chloro-succinimide; triphenylphosphine In 1,4-dioxane at 100℃; for 1h; 207.3 Step 3. Synthesis of ethyl 6-bromo-3-chloro-5-methylpyrazine-2-carboxylate A 500 mL flask was charged with triphenylphosphine (18.0 g, 68.7 mmol, 3 equiv) and 1,4-dioxane (228 mL). N-Chlorosuccinimide (9.32 g, 69.8 mmol, 3.05 equiv) was then added to this solution, and the resulting mixture was left to stir for 30 min at room temperature. Ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate (6 g, 22.9 mmol, 1 equiv) was added in one portion, and the resulting mixture was warmed to 100 °C and allowed to stir for 1 hour. The reaction was then cooled to room temperature, triethylamine (57 mL) was added to the reaction mixture. This crude material was dissolved in DCM and passed through a silica gel plug (elution with 5 to 10% EtOAc-Heptane) This solid was further purified by column chromatography to give ethyl 6-bromo-3-chloro-5-methylpyrazine-2-carboxylate (5.20 g, 18.6 mmol, 81.2%) as an orange solid. 1H NMR (500 MHz, chloroform- ) δ 4.48 (q, J = 5.0, 10.0 Hz, 2H), 2.72 (s, 3H), 1.43 (t, J = 7.5 Hz, 3H). LC-MS (ESI): calculated for C8H9BrClN202 [M + H] m/z 278.9, found 278.9.
6.66 g With N-chloro-succinimide; triphenylphosphine In 1,4-dioxane at 100℃; for 1h; 1 To a solution of PPh 3 (31.03 g, 80.18 mmol) in 1, 4-dioxane (280 mL) was added NCS (10.77 g, 80.66 mmol) . The resulting mixture was stirred for 30 min at RT. Compound 1-2 (6.96 g, 26.66 mmol) was added, the resulting mixture was warmed to 100 and stirred for 1H. After cooling to RT, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting with EA : Hex = 1 : 5, v/v) to give compound 1-3 (6.66 g) as a yellow oil. MS: 279 [M+1] +.
5.1g With N-chloro-succinimide; triphenylphosphine In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; 1.3 Step 3: ethyl 6-bromo-3-chloro-5-methylpyrazine-2-carboxylate Triphenylphosphine (21.1g) and NCS (10.8g) were added into 1,4-dioxane (100mL), and reacted at room temperature for 0.5 hour. Then ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate (7.0g) was added into the solution and reacted at 100 °C for 1 hour under N2 protection. The reaction mixture was poured into water (300mL) and extracted by dichloromethane (100mL) for 3 times. The organic phase was dried by anhydrous sodium sulfate, and crude product was obtained after removal of solvent. Final product (5.1g) was obtained after purification by column chromatography. LC-MS, (ES, m/z): [M+H]+ = 279.
5.1g With N-chloro-succinimide; triphenylphosphine In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; 1.3 Step 3: ethyl 6-bromo-3-chloro-5-methylpyrazine-2-carboxylate Triphenylphosphine (21.1g) and NCS (10.8g) were added into 1,4-dioxane (100mL), and reacted at room temperature for 0.5 hour. Then ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate (7.0g) was added into the solution and reacted at 100 °C for 1 hour under N2 protection. The reaction mixture was poured into water (300mL) and extracted by dichloromethane (100mL) for 3 times. The organic phase was dried by anhydrous sodium sulfate, and crude product was obtained after removal of solvent. Final product (5.1g) was obtained after purification by column chromatography. LC-MS, (ES, m/z): [M+H]+ = 279.

  • 6
  • [ 1269026-22-3 ]
  • ethyl 3-chloro-6-(3-chloro-2-methoxypyridin-4-yl)-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; acetonitrile / 1 h / 100 °C / Inert atmosphere
  • 7
  • [ 1269026-22-3 ]
  • ethyl 3-(4-((tert-butoxycarbonyl)amino)-4-methylpiperidin-1-yl)-6-(3-chloro-2-methoxypyridin-4-yl)-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; acetonitrile / 1 h / 100 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 0.5 h / 100 °C
  • 8
  • [ 1269026-22-3 ]
  • (3-(4-amino-4-methylpiperidin-1-yl)-6-(3-chloro-2-methoxypyridin-4-yl)-5-methylpyrazin-2-yl)methanol formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; acetonitrile / 1 h / 100 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 0.5 h / 100 °C 4: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C
  • 9
  • [ 1269026-22-3 ]
  • ethyl 3-((3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl)-6-bromo-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C
  • 10
  • [ 1269026-22-3 ]
  • (3-((3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl)-6-bromo-5-methylpyrazin-2-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C 3: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C
  • 11
  • [ 1269026-22-3 ]
  • {3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-5-methyl-6-(2-methyl-1,3-benzoxazol-6-yl)pyrazin-2-yl}methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C 3: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / acetonitrile / 1.5 h / 100 °C / Inert atmosphere
  • 12
  • [ 1269026-22-3 ]
  • {3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-5-methyl-6-(1-methyl-1H-indol-2-yl)pyrazin-2-yl}methanol formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C 3: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C 4: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol / 16 h / 80 °C / Inert atmosphere
  • 13
  • [ 1269026-22-3 ]
  • ethyl 3-chloro-6-(2,3-dichlorophenyl)-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate / acetonitrile / 1 h / 100 °C
Multi-step reaction with 2 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / acetonitrile; lithium hydroxide monohydrate / 2.5 h / 100 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 80 °C / Inert atmosphere 2: trichlorophosphate / 120 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: triphenylphosphine; aminomethanethiol 2: potassium carbonate
Multi-step reaction with 2 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / acetonitrile / 90 °C / Inert atmosphere

  • 14
  • [ 1269026-22-3 ]
  • ethyl 3-((3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl)-6-(2,3-dichlorophenyl)-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / acetonitrile / 1 h / 100 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 55 °C
  • 15
  • [ 1269026-22-3 ]
  • {3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-(2,3-dichlorophenyl)-5-methylpyrazin-2-yl}methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / acetonitrile / 1 h / 100 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 55 °C 4: diisobutylaluminium hydride / dichloromethane / -78 °C / Heating
  • 16
  • [ 1269026-22-3 ]
  • ethyl 6-bromo-3-((3S,4S)-4-((tert-butoxycarbonyl)amino)-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl)-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 23 h / 85 °C / Inert atmosphere 2.2: 1 h / 23 °C
  • 17
  • [ 1269026-22-3 ]
  • tert-butyl ((3S,4S)-8-(3-(hydroxymethyl)-6-methyl-5-(3-methyl-1H-indazol-6-yl)pyrazin-2-yl)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 23 h / 85 °C / Inert atmosphere 2.2: 1 h / 23 °C 3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - -40 °C 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol / 80 °C / Sealed tube
  • 18
  • [ 1269026-22-3 ]
  • (3-((3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl)-5-methyl-6-(3-methyl-1H-indazol-6-yl)pyrazin-2-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 23 h / 85 °C / Inert atmosphere 2.2: 1 h / 23 °C 3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - -40 °C 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol / 80 °C / Sealed tube 5.1: trifluoroacetic acid / dichloromethane / 20 °C
  • 19
  • [ 1269026-22-3 ]
  • (R)-tert-butyl (8-(3-(hydroxymethyl)-6-methyl-5-((1-methyl-1H-indol-7-yl)thio)pyrazin-2-yl)-8-azaspiro[4.5]decan-1-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 23 h / 85 °C / Inert atmosphere 2.2: 1 h / 23 °C 3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - -40 °C 4.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 120 °C / Inert atmosphere; Microwave irradiation
  • 20
  • [ 1269026-22-3 ]
  • {3-[(1R)-1-amino-8-azaspiro[4.5]decan-8-yl]-5-methyl-6-[(1-methyl-1H-indol-7-yl)sulfanyl]pyrazin-2-yl}methanol formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 23 h / 85 °C / Inert atmosphere 2.2: 1 h / 23 °C 3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - -40 °C 4.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 120 °C / Inert atmosphere; Microwave irradiation 5.1: hydrogenchloride / 1,4-dioxane; methanol / 3 h
  • 21
  • [ 1269026-22-3 ]
  • tert-butyl ((3S,4S)-8-(5-((3-chloro-2-((tetrahydro-2H-pyran-4-yl)amino)pyridin-4-yl)thio)-3-(hydroxymethyl)-6-methylpyrazin-2-yl)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 23 h / 85 °C / Inert atmosphere 2.2: 1 h / 23 °C 3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - -40 °C 4.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / Inert atmosphere; Microwave irradiation; Heating
  • 22
  • [ 1269026-22-3 ]
  • (3-((3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl)-6-((3-chloro-2-((tetrahydro-2H-pyran-4-yl)amino)pyridin-4-yl)thio)-5-methylpyrazin-2-yl)methanol formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 23 h / 85 °C / Inert atmosphere 2.2: 1 h / 23 °C 3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - -40 °C 4.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / Inert atmosphere; Microwave irradiation; Heating 5.1: hydrogenchloride / 1,4-dioxane; methanol / 0.5 h / 50 °C
  • 23
  • [ 1269026-22-3 ]
  • tert-butyl ((3S,4S)-8-(5-((3-chloro-2-((tetrahydro-2H-pyran-4-yl)oxy)pyridin-4-yl)thio)-3-(hydroxymethyl)-6-methylpyrazin-2-yl)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 23 h / 85 °C / Inert atmosphere 2.2: 1 h / 23 °C 3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - -40 °C 4.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / Inert atmosphere; Heating; Microwave irradiation
  • 24
  • [ 1269026-22-3 ]
  • (3-((3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl)-6-((3-chloro-2-((tetrahydro-2H-pyran-4-yl)oxy)pyridin-4-yl)thio)-5-methylpyrazin-2-yl)methanol formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 23 h / 85 °C / Inert atmosphere 2.2: 1 h / 23 °C 3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - -40 °C 4.1: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / Inert atmosphere; Heating; Microwave irradiation 5.1: hydrogenchloride / 1,4-dioxane; methanol / 0.5 h / 50 °C
  • 25
  • [ 1269026-22-3 ]
  • 1-(4-((5-((3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl)-6-(hydroxymethyl)-3-methylpyrazin-2-yl)thio)-3-chloropyridin-2-yl)azetidine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C 3: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C 4: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 120 °C / Inert atmosphere; Microwave irradiation
  • 26
  • [ 1269026-22-3 ]
  • {3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-[3-chloro-2-(1H-imidazol-1-yl)pyridin-4-yl]sulfanyl}-5-methylpyrazin-2-yl}methanol formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C 3: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C 4: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 120 °C / Inert atmosphere; Microwave irradiation
  • 27
  • [ 1269026-22-3 ]
  • {3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-[3-chloro-2-(methylamino)pyridin-4-yl]sulfanyl}-5-methylpyrazin-2-yl}methanol formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C 3: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C 4: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 2 h / Inert atmosphere; Microwave irradiation; Heating
  • 28
  • [ 1269026-22-3 ]
  • {6-[(2-amino-3-chloropyridin-4-yl)sulfanyl]-3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-5-methylpyrazin-2-yl}methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C 3: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C 4: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 2 h / Inert atmosphere; Microwave irradiation; Heating
  • 29
  • [ 1269026-22-3 ]
  • {3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-[(3-chloro-2-cyclopropoxypyridin-4-yl)sulfanyl]-5-methylpyrazin-2-yl}methanol formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C 3: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C 4: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); lithium diisopropyl amide / 1,4-dioxane / 2 h / 110 °C / Inert atmosphere; Microwave irradiation
  • 30
  • [ 1269026-22-3 ]
  • {3-[(3S,4S)-4-amino-3-methyl-2-oxa-8-azaspiro[4.5]decan-8-yl]-6-[2,3-dichloro-6-(methylamino)pyridin-4-yl]-5-methylpyrazin-2-yl}methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C 3: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / acetonitrile / 3 h / 100 °C / Inert atmosphere; Microwave irradiation 5: hydrogenchloride / 1,4-dioxane; methanol / 20 °C
  • 31
  • [ 1269026-22-3 ]
  • C26H36Cl2N6O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 12 h / 55 °C 3: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / acetonitrile / 3 h / 100 °C / Inert atmosphere; Microwave irradiation
  • 32
  • [ 1269026-22-3 ]
  • tert-butyl N-(1-{5-bromo-6-methylimidazo[1,2-a]pyrazin-8-yl}-4-methylpiperidin-4-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: water / 1 h / 25 - 120 °C 5: triethylamine; trichlorophosphate / 0.5 h / Heating 6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C / Sealed tube
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: potassium carbonate; methanol / 15 h / 70 °C 5: water / 1 h / 25 - 120 °C 6: triethylamine; trichlorophosphate / 0.5 h / Heating 7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C / Sealed tube
  • 33
  • [ 1269026-22-3 ]
  • tert-butyl N-{1-[5-(2,3-dichlorophenyl)-6-methylimidazo[1,2-a]pyrazin-8-yl]-4-methylpiperidin-4-yl}carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: water / 1 h / 25 - 120 °C 5: triethylamine; trichlorophosphate / 0.5 h / Heating 6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C / Sealed tube 7: palladium diacetate; potassium phosphate / 1,4-dioxane / 2 h / 105 °C / Inert atmosphere
Multi-step reaction with 8 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: potassium carbonate; methanol / 15 h / 70 °C 5: water / 1 h / 25 - 120 °C 6: triethylamine; trichlorophosphate / 0.5 h / Heating 7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C / Sealed tube 8: palladium diacetate; potassium phosphate / 1,4-dioxane / 2 h / 105 °C / Inert atmosphere
  • 34
  • [ 1269026-22-3 ]
  • 6-bromo-3-[(4-methoxyphenyl)methoxy]-5-methylpyrazin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: potassium carbonate; methanol / 15 h / 70 °C
  • 35
  • [ 1269026-22-3 ]
  • 5-bromo-6-methylimidazo[1,2-a]pyrazin-8-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: water / 1 h / 25 - 120 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: potassium carbonate; methanol / 15 h / 70 °C 5: water / 1 h / 25 - 120 °C
  • 36
  • [ 1269026-22-3 ]
  • 5-bromo-8-chloro-6-methylimidazo[1,2-a]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: water / 1 h / 25 - 120 °C 5: triethylamine; trichlorophosphate / 0.5 h / Heating
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: potassium carbonate; methanol / 15 h / 70 °C 5: water / 1 h / 25 - 120 °C 6: triethylamine; trichlorophosphate / 0.5 h / Heating
  • 37
  • [ 1269026-22-3 ]
  • (3S,4S)-8-(5-bromo-6-methylimidazo[1,2-a]pyrazin-8-yl)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: water / 1 h / 25 - 120 °C 5: triethylamine; trichlorophosphate / 0.5 h / Heating 6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: potassium carbonate; methanol / 15 h / 70 °C 5: water / 1 h / 25 - 120 °C 6: triethylamine; trichlorophosphate / 0.5 h / Heating 7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C
  • 38
  • [ 1269026-22-3 ]
  • (3S,4S)-8-(5-((2-amino-3-chloropyridin-4-yl)thio)-6-methylimidazo[1,2-a]pyrazin-8-yl)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: water / 1 h / 25 - 120 °C 5: triethylamine; trichlorophosphate / 0.5 h / Heating 6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C 7: N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 140 °C / Inert atmosphere
Multi-step reaction with 8 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: potassium carbonate; methanol / 15 h / 70 °C 5: water / 1 h / 25 - 120 °C 6: triethylamine; trichlorophosphate / 0.5 h / Heating 7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C 8: N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 140 °C / Inert atmosphere
  • 39
  • [ 1269026-22-3 ]
  • (3S,4S)-8-(5-(3-chlorophenyl)-6-methylimidazo[1,2-a]pyrazin-8-yl)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: water / 1 h / 25 - 120 °C 5: triethylamine; trichlorophosphate / 0.5 h / Heating 6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C 7: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / acetonitrile / 2 h / 105 °C / Inert atmosphere
Multi-step reaction with 8 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: potassium carbonate; methanol / 15 h / 70 °C 5: water / 1 h / 25 - 120 °C 6: triethylamine; trichlorophosphate / 0.5 h / Heating 7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C 8: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / acetonitrile / 2 h / 105 °C / Inert atmosphere
  • 40
  • [ 1269026-22-3 ]
  • (3S,4S)-8-(5-(2,3-dichlorophenyl)-6-methylimidazo[1,2-a]pyrazin-8-yl)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: water / 1 h / 25 - 120 °C 5: triethylamine; trichlorophosphate / 0.5 h / Heating 6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C 7: palladium diacetate; potassium phosphate / 1,4-dioxane / 125 °C / Sealed tube
Multi-step reaction with 8 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: potassium carbonate; methanol / 15 h / 70 °C 5: water / 1 h / 25 - 120 °C 6: triethylamine; trichlorophosphate / 0.5 h / Heating 7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C 8: palladium diacetate; potassium phosphate / 1,4-dioxane / 125 °C / Sealed tube
  • 41
  • [ 1269026-22-3 ]
  • 1-[5-(2,3-dichlorophenyl)-6-methylimidazo[1,2-a]pyrazin-8-yl]-4-methylpiperidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: water / 1 h / 25 - 120 °C 5: triethylamine; trichlorophosphate / 0.5 h / Heating 6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C / Sealed tube 7: palladium diacetate; potassium phosphate / 1,4-dioxane / 2 h / 105 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; methanol / 4 h / Sealed tube
Multi-step reaction with 9 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: lithium hydroxide; water / methanol / 15 h / 25 °C 3: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 110 °C / Inert atmosphere 4: potassium carbonate; methanol / 15 h / 70 °C 5: water / 1 h / 25 - 120 °C 6: triethylamine; trichlorophosphate / 0.5 h / Heating 7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 100 °C / Sealed tube 8: palladium diacetate; potassium phosphate / 1,4-dioxane / 2 h / 105 °C / Inert atmosphere 9: hydrogenchloride / 1,4-dioxane; methanol / 4 h / Sealed tube
  • 42
  • [ 1269026-22-3 ]
  • [ 824-94-2 ]
  • ethyl 6-bromo-3-[(4-methoxyphenyl)methoxy]-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60 g With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2h; Inert atmosphere; 6.3 [00707] To a solution of ethyl 6-bromo-3-hydroxy-5-methyl-pyrazine-2-carboxylate (115 g, 440.49 mmol) and K2CO3 (182.64 g, 1.32 mol) in DMF (2.1 L) was added PMB-C1 (103.48 g, 660.74 mmol, 89.98 mL) in one portion at 20 °C under N2. The mixture was stirred at 50 °C for 2 hr. The resulting mixture was diluted with water and the aqueous phase was extracted with EtOAc. The combined organic phase was washed with brine (200 mL), dried with anhydrous Na2S04, and concentrated under reduced pressure. The remaining residue was purified by column chromatography to afford ethyl 6-bromo-3-[(4- methoxyphenyl)methoxy]-5-methyl-pyrazine-2-carboxylate (60 g, 35.73% yield) as a white solid. LCMS (ESI): m/z [M +Na] calculated for 403.04; found 403.1.
  • 43
  • [ 1269026-22-3 ]
  • [ 151169-74-3 ]
  • ethyl 6-(2,3-dichlorophenyl)-3-hydroxy-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere; Ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate (2.5 g, 9.58 mmol), 2,3-dichlorophenylboronic acid (2.7 g, 14.15 mmol), Pd(dppf)Cl2 (690 mg, 0.94 mmol) and potassium carbonate (2.6 g, 18.81 mmol) were dissolved in anhydrous dioxane (50 mL)/ water (10 mL). The reaction solution was purged with nitrogen, heated to 80C and stirred overnight. The reaction solution was cooled to room temperature, and then water was added. The solution was extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to obtain a crude product, which was purified by column chromatography to obtain the product ethyl 6-(2,3-dichlorophenyl)-3-hydroxy-5-methylpyrazine-2-carboxylate (2.0 g, yield: 64%).MS m/z (ESI): 327.0 [M+H]+, 329.0[M+2+H]+.
29% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In water; acetonitrile; at 90℃; for 1h;Inert atmosphere; To the stirred mixture of ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate (1.90 g, 7.28 mmol, 1.00 eq) and K2C03 (4.02 g, 29.1 mmol, 4 eq) in ACN (9.50 mL) and H20 (1.90 mL) was added (2,3-dichlorophenyl)boronic acid (1.39 g, 7.28 mmol, 1.00 eq) and Pd(dppf)Cl2 CH2Cl2 (594 mg, 728 umol, 0.10 eq) under N2 at 20 C. The mixture was stirred at 90 C for 1 h. To the mixture was then added H20 (20.0 mL) and acidified with 0.5 N HC1 to pH = 7. The mixture was then extracted with ethyl acetate (40.0 mL x 3). The combined organic layers were washed with brine (30.0 mL x 2), dried over Na2S04, filtered and concentrated. The residue was purified by flash silica gel chromatography (petroleum ether/ethyl acetate=50/l~l/l, Rf = 0.6) to give ethyl 6-(2,3-dichlorophenyl)-3-hydroxy-5- methylpyrazine-2-carboxylate (700 mg, 29% yield) as a yellow solid. LCMS m/z [M+H]+ = 327.1; 1H MR (400MHz CDCl3) 11.47 (br s, 1 H), 7.57 (d, J= 7.6 Hz, 1 H), 7.34 (t, J= 7.6 Hz, 1 H), 7.27 - 7.25 (m, 1 H), 4.56 (q, J = 6.8 Hz, 2 H), 2.42 (s, 3 H), 1.45 (td, J = 7.2 Hz, 0.8 Hz, 3 H).
  • 44
  • [ 1269026-22-3 ]
  • (S)-ethyl 3-(1-amino-1,3-dihydrospiro[indene-2,4'-piperidin]-1'-yl)-6-(2,3-dichlorophenyl)-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / acetonitrile; lithium hydroxide monohydrate / 2.5 h / 100 °C / Inert atmosphere 3: potassium carbonate / acetonitrile / 24 h / 100 °C
Multi-step reaction with 3 steps 1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 80 °C / Inert atmosphere 2: trichlorophosphate / 120 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / acetonitrile / 90 °C / Inert atmosphere 3: potassium carbonate; 1-Methylpyrrolidine / 100 °C 4: hydrogenchloride / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 20 °C
  • 45
  • [ 1269026-22-3 ]
  • (S)-(3-(1-amino-1,3-dihydrospiro[indene-2,4'-piperidin]-1'-yl)-6-(2,3-dichlorophenyl)-5-methylpyrazin-2-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C 2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / acetonitrile; lithium hydroxide monohydrate / 2.5 h / 100 °C / Inert atmosphere 3: potassium carbonate / acetonitrile / 24 h / 100 °C 4: lithium tetrahydridoborate / tetrahydrofuran / 16 h / 0 - 70 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate / 1,4-dioxane; lithium hydroxide monohydrate / 80 °C / Inert atmosphere 2: trichlorophosphate / 120 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C / Inert atmosphere 4: diisobutylaluminium hydride / dichloromethane / 2.5 h / -78 - 20 °C / Inert atmosphere
Multi-step reaction with 5 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / acetonitrile / 90 °C / Inert atmosphere 3: potassium carbonate; 1-Methylpyrrolidine / 100 °C 4: hydrogenchloride / 1,4-dioxane; lithium hydroxide monohydrate / 4 h / 20 °C 5: diisobutylaluminium hydride / tetrahydrofuran / -78 - 20 °C
  • 46
  • [ 24424-99-5 ]
  • [ 1269026-22-3 ]
  • (3S,4S)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine bishydrochloride [ No CAS ]
  • 6-bromo-3-((3S,4S)-4-(tert-butoxycarbonylamino)-3-methyl-2-oxa-8-azaspiro[4.5]dec-8-yl)-5-methylpyrazine-2-carboxylate ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate; (3S,4S)-3-methyl-2-oxa-8-azaspiro[4.5]decan-4-amine bishydrochloride With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; for 2h; Stage #2: di-<i>tert</i>-butyl dicarbonate In N,N-dimethyl-formamide for 2h; first step: Preparation of 6-Bromo-3-((3S,4S)-4-(tert-butoxycarbonylamino)-3-methyl-2-oxa-8-azaspiro[4.5]dec-8-yl)-5- Methylpyrazine-2-carboxylate ethyl ester (B-2) After mixing compound B-0 (200 mg, 766.07 umol), DMF (4 mL), compound B-1 (195.60 mg, 804.37 umol), BOP (312.74 mg, 1.53 mmol) and DIPEA (594.04 mg, 4.60 mmol), the temperature was increased. to 40°C, and reacted for 2 hours. After the reaction was completed, di-tert-butyl dicarbonate (250.79 mg, 1.15 mmol) was added, and the reaction was continued for 2 hours. Water and ethyl acetate were added for extraction, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain a crude product. The crude product was purified by thin layer chromatography to give compound B-2 (290 mg, yield 73%).
  • 47
  • [ 1269026-22-3 ]
  • ethyl 6-(2-(N,N-di(tert-butoxycarbonyl) amino)-3-chloropyridin-4-yl)-3-chloro-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; aminomethanethiol 2: potassium carbonate
Multi-step reaction with 2 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / acetonitrile / 90 °C / Inert atmosphere
  • 48
  • [ 1269026-22-3 ]
  • ethyl 3-chloro-5-methyl-6-(2-(trifluoromethyl)pyridin-3-yl)pyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; aminomethanethiol 2: potassium carbonate
Multi-step reaction with 2 steps 1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / acetonitrile / Inert atmosphere; Reflux
  • 49
  • [ 1269026-22-3 ]
  • ethyl 6-(6-((tert-butoxycarbonyl)amino)-2,3-dichloropyridin-4-yl)-3-chloro-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; aminomethanethiol 2: tetrakis-(triphenylphosphine)-palladium
Multi-step reaction with 2 steps 1.1: triphenylphosphine; N-chloro-succinimide / 1,4-dioxane / 1 h / 100 °C / Inert atmosphere 2.1: lithium dipropan-2-ylazanide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: 1 h / 20 °C 2.3: 1 h / 80 °C / Inert atmosphere
  • 50
  • [ 123-91-1 ]
  • [ 1269026-22-3 ]
  • ethyl 6-bromo-3-chloro-5-methylpyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With aminomethanethiol; triphenylphosphine 1.3 Step 3: Step 3: ethyl 6-bromo-3-chloro-5-methylpyrazine-2-carboxylate Triphenylphosphine (21.1g) and NCS (10.8g) were added into 1,4-dioxane (100mL), and reacted at room temperature for 0.5 hour. Then ethyl 6-bromo-3-hydroxy-5-methylpyrazine-2-carboxylate (7.0g) was added into the solution and reacted at 100 °C for 1 hour under N2 protection. The reaction mixture was poured into water (300mL) and extracted by dichloromethane (100mL) for 3 times. The organic phase was dried by anhydrous sodium sulfate, and crude product was obtained after removal of solvent. Final product (5.1g) was obtained after purification by column chromatography. LC-MS, (ES, m/z): [M+H]+ = 279.
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