Home Cart 0 Sign in  

[ CAS No. 1630907-10-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1630907-10-6
Chemical Structure| 1630907-10-6
Structure of 1630907-10-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1630907-10-6 ]

Related Doc. of [ 1630907-10-6 ]

Alternatived Products of [ 1630907-10-6 ]

Product Details of [ 1630907-10-6 ]

CAS No. :1630907-10-6 MDL No. :MFCD23703064
Formula : C6H12ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :GVISYHVUGUIQRD-UHFFFAOYSA-N
M.W :149.62 Pubchem ID :73554122
Synonyms :

Safety of [ 1630907-10-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1630907-10-6 ]

* 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 [ 1630907-10-6 ]

[ 1630907-10-6 ] Synthesis Path-Downstream   1~23

  • 1
  • [ 2403798-88-7 ]
  • [ 1630907-10-6 ]
  • [ 2403800-39-3 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate In N,N-dimethyl acetamide at 70℃; for 18h; 303.a 5-[(3R)-3-hydroxypyrrolidin-l-yl]-2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4- yl] methyl]pyridazin-3-one General procedure: To a stirred suspension of 5-chloro-2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4- yl]methyl]pyridazin-3-one (building block A, 300 mg, 0.947 mmol) and (R)-3- hydroxypyrrolidine (0.14 mL, 1.73 mmol) in DMSO (0.5 mL) and acetonitrile (3 mL) was added potassium carbonate (393 mg, 2.84 mmol) Then the reaction mixture was stirred at 70 °C for 18 h. After cooling to room temperature the reaction mixture was diluted with EtOAc (80 mL) was washed three times with water (10 mL) and brine (10 mL). The aqueous layers were back extracted twice with EtOAc (80 mL). The combined organic extracts were dried (Na2S04), filtered and concentrated in vacuo. Purification by flash chromatography (silica, gradient: 0% to 10% MeOH in CH2CI2) afforded the title compound (341 mg, 93 %) as an off-white foam. MS (ESI): 368.2 ([M+H]+).
  • 2
  • [ 2403798-92-3 ]
  • [ 1630907-10-6 ]
  • [ 2403800-40-6 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In acetonitrile at 80℃; for 18h; Inert atmosphere; 315.a 5-(4-hydroxy-l-piperidyl)-2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4- yl] methyl] pyridazin-3-one General procedure: To a stirred solution of 5-chloro-2-[[5-methyl-3-(6-methyl-3-pyridyl)isoxazol-4- yl]methyl]pyridazin-3-one (building block A, 51.2 mg, 0.162 mmol) in acetonitrile (1 mL) under an atmosphere of argon was added potassium carbonate (67 mg, 0.49 mmol) and piperidin-4-ol (24.5 mg, 0.242 mmol). The vial was capped and heated to 80 °C for 18 h. After cooling to room temperature the reaction mixture was diluted with EtOAc (20 mL) and was washed with water (15 mL) and brine (15 mL). The aqueous layers were extracted twice with EtOAc (20 mL). The combined organic extracts were dried (MgS04), filtered and concentrated in vacuo. Purification by flash chromatography (silica, gradient: 0% to 10% MeOH in CH2CI2) afforded the title compound (341 mg, 93 %) as an off-white foam. MS (ESI): 382.3 ([M+H]+).
  • 3
  • [ 1630907-10-6 ]
  • [ 100-52-7 ]
  • [ 1822863-35-3 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 2-azaspiro[3.3]heptan-6-ol hydrochloride; benzaldehyde With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In 1,2-dichloro-ethane Inert atmosphere; 10 Example 10: Preparation of 2-benzyl-2-azaspiro[3.3]heptan-6-ol (Intermediate 10A) To a suspension of 2-azaspiro[3.3]heptan-6-ol hydrochloride (4.6 g, 30.7 mmol, 1.0 eq) in dichloroethane (160 mL) was added benzaldehyde (4.6 mL, 46.0 mmol, 1.5 eq) followed by sodium triacetoxyborohydride (32 g, 153 mmol, 5.0 eq). The resulting mixture was stirred at room temperature overnight. The formed suspension was carefully diluted and stirred with sat. NaHCO3 until the evolution of hydrogen ceased. The aqueous mixture was extracted with 5:1 DCM:2-propanol. The combined organic layers were dried over MgSO4, filtered to remove solid and concentrated in vacuo. The crude material was purified by silica gel column (120 g) using DCM and run with an increasing gradient of MeOH (0-20%) in DCM over 20 min, flushing with 50% MeOH to provide 2-benzyl-2-azaspiro[3.3]heptan-6-ol (Intermediate 10A, 6.1 g, 30.0 mmol, 98%) as an orange liquid.
  • 4
  • [ 1630907-10-6 ]
  • [ 2682992-60-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: acetonitrile / 1 h / 20 °C / Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 80 °C / Inert atmosphere
  • 5
  • [ 1630907-10-6 ]
  • [ 2682992-88-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 2.2: 20 °C
  • 6
  • [ 1630907-10-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere
  • 7
  • [ 1630907-10-6 ]
  • [ 2682993-14-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 2.2: 50 °C 3.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 50 °C / Inert atmosphere
  • 8
  • [ 1630907-10-6 ]
  • [ 2682993-29-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 2.2: 50 °C 3.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 4.1: sodium t-butanolate / toluene / 2 h / 90 °C / Inert atmosphere
  • 9
  • [ 1630907-10-6 ]
  • [ 2682998-47-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 2.2: 50 °C
  • 10
  • [ 1630907-10-6 ]
  • [ 2682998-46-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere 2.2: 50 °C 3.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere
  • 11
  • [ 1630907-10-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: dichloromethane / 20 °C / Inert atmosphere 2.2: 20 - 40 °C / Inert atmosphere
  • 12
  • [ 1630907-10-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: acetonitrile / 1 h / 20 °C / Inert atmosphere
  • 13
  • [ 1630907-10-6 ]
  • [ 2683585-48-8 ]
  • [ 2683585-61-5 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: (S)-tert-butyl ((6-(2,2'-dichloro-3'-(2-(hydroxymethyl)-3-methyl-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-6-yl)-[1,1'-biphenyl]-3-yl)-2-methoxypyridin-3-yl)methyl)((5-oxopyrrolidin-2-yl)methyl)carbamate With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 1h; Stage #2: 2-azaspiro[3.3]heptan-6-ol hydrochloride With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h; 468 tert- Butyl N- [ [6- [2-chlor o-3- [2-chloro-3- [2- [(6-hydroxy-2-azaspir o [3.3] heptan-2- yl)methyl]-3-methyl-4-oxo-pyrrolo[2,l-f|[l,2,4]triazin-6-yl]phenyl]phenyl]-2-methoxy-3- pyridyl]methyl]-N-[[(2S)-5-oxopyrrolidin-2-yl]methyl]carbamate To a solution of tert- butyl N-[[6-[2-chloro-3-[2-chloro-3-[2-(hydroxymethyl)-3-methyl-4- oxo-pyrrolo[2,l-f][l,2,4]triazin-6-yl]phenyl]phenyl]-2-methoxy-3-pyridyl]methyl]-N-[[(2S)- 5-oxopyrrolidin-2-yl]methyl]carbamate (20 mg, 0.03 mmol) in DCM (0.1 mL) was added mesyl chloride (2.3 uL, 0.03 mmol) and triethylamine (7.6 uL, 0.05 mmol). The reaction was stirred at rt for lh. The solvent was evaporated, and the residue was suspended in DMF (0.4 mL). To this suspension, potassium carbonate (10 mg, 0.07 mmol) and 2- azaspiro[3.3]heptan-6-ol, HC1 (11 mg, 0.07 mmol) was added The reaction was heated to 60 °C for 3h. The solvent was evaporated, and the residue was suspended in water. The solid formed was collected by filtration to afford /cvV-butyl N-[[6-[2-chloro-3-[2-chloro-3-[2-[(6- hydroxy-2-azaspiro[3.3]heptan-2-yl)methyl]-3-methyl-4-oxo-pyrrolo[2,l-f][l,2,4]triazin-6- yl]phenyl]phenyl]-2-methoxy-3-pyridyl]methyl]-N-[[(2S)-5-oxopyrrolidin-2- yl]methyl]carbamate (16 mg, 78%). The material was used as is for the next step m/z: 830.3 [M+H]+ observed.
  • 14
  • [ 1630907-10-6 ]
  • [ 2683586-21-0 ]
  • [ 2683586-44-7 ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate In N,N-dimethyl-formamide at 30℃; for 12h; Inert atmosphere; 517 2-Bromo-5-((6-hydroxy-2-azaspiro[3.3]heptan-2-yl)methyl)-l-methylpyrazolo[l,5- a]pyrimidin-7(lH)-one: To a mixture of 2-bromo-5-(chloromethyl)-l-methylpyrazolo[l,5-a]pyrimidin-7(lH)-one (0.3 g, 1.08 mmol) and 2-azaspiro[3.3]heptan-6-ol as a hydrochloride salt (0.18 g, 1.19 mmol) in DMF (4 mL) was added potassium carbonate (0.45 g, 3.25 mmol) in one portion under N2 atmosphere. The mixture was stirred at 30 °C for 12 h. The mixture was concentrated. The residue was purified by normal phase S1O2 chromatography (0-80% MeOH/ethyl acetate) to afford 2-bromo-5-((6-hydroxy-2-azaspiro[3.3]heptan-2-yl)methyl)-l-methylpyrazolo[l,5- a]pyrimidin-7(lH)-one as a yellow solid (0.3 g, 48% yield). MS: m/z found 353 [M+H]+.
  • 15
  • [ 1214336-88-5 ]
  • [ 1630907-10-6 ]
  • [ 2758668-90-3 ]
YieldReaction ConditionsOperation in experiment
500.0 mg With potassium carbonate In acetonitrile at 80℃; Step 2: methyl 5-fluoro-6-[6-hydroxy-2-azaspiro[3.3]heptan-2-yl]pyridine-3-carboxylate Methyl 6-bromo-5-fluoropyridine-3-carboxylate (2.1 g, 8.8 mmol, 1.0 equiv.) and 2-azaspiro[3.3]heptan-6-ol hydrochloride (1.0 g, 8.8 mmol, 1.0 equiv.) were dissolved in ACN (20 mL), then K2CO3 (3.7 g, 26.5 mmol, 3.0 equiv.) was added. The reaction mixture was heated to 80 °C overnight, then cooled to ambient temperature and quenched by the addition of water. The resulting solution was extracted with ethyl acetate, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by Flash-Prep-HPLC using the following conditions: Column, C18 silica gel; mobile phase, H2O/ACN; 10% ACN increasing to 90% within 30 min; Detector, 254 nm. This gave methyl 5-fluoro-6-[6-hydroxy-2-azaspiro[3.3]heptan-2-yl]pyridine-3-carboxylate (500.0 mg) as a yellow solid. LCMS Method A-1: [M+H]+ = 267.
500.0 mg With potassium carbonate In acetonitrile at 80℃; Step 2: methyl 5-fluoro-6-[6-hydroxy-2-azaspiro[3.3]heptan-2-yl]pyridine-3-carboxylate Methyl 6-bromo-5-fluoropyridine-3-carboxylate (2.1 g, 8.8 mmol, 1.0 equiv.) and 2-azaspiro[3.3]heptan-6-ol hydrochloride (1.0 g, 8.8 mmol, 1.0 equiv.) were dissolved in ACN (20 mL), then K2CO3 (3.7 g, 26.5 mmol, 3.0 equiv.) was added. The reaction mixture was heated to 80 °C overnight, then cooled to ambient temperature and quenched by the addition of water. The resulting solution was extracted with ethyl acetate, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by Flash-Prep-HPLC using the following conditions: Column, C18 silica gel; mobile phase, H2O/ACN; 10% ACN increasing to 90% within 30 min; Detector, 254 nm. This gave methyl 5-fluoro-6-[6-hydroxy-2-azaspiro[3.3]heptan-2-yl]pyridine-3-carboxylate (500.0 mg) as a yellow solid. LCMS Method A-1: [M+H]+ = 267.
  • 16
  • [ 1147557-97-8 ]
  • [ 1630907-10-6 ]
YieldReaction ConditionsOperation in experiment
1.0 g With hydrogenchloride In 1,4-dioxane at 20℃; Step 1: 2-azaspiro[3.3]heptan-6-ol hydrochloride tert-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (1.6 g, 7.5 mmol, 1.0 equiv.) was dissolved in HCl/1,4-dioxane (4 M, 20 mL). The reaction mixture was stirred overnight at ambient temperature, then concentrated under vacuum to give 2-azaspiro[3.3]heptan-6-ol hydrochloride (1.0 g) as a yellow oil. LCMS Method A-1: [M+H]+ = 114.
  • 17
  • [ 1630907-10-6 ]
  • [ 2758668-91-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 80 °C 2: triethylamine / dichloromethane / 2 h
  • 18
  • [ 1630907-10-6 ]
  • [ 2758668-89-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 80 °C 2: triethylamine / dichloromethane / 2 h 3: N,N-dimethyl-formamide / 80 °C
  • 19
  • [ 1630907-10-6 ]
  • [ 2682003-69-4 ]
  • [ 2757310-92-0 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 2.5h; Inert atmosphere; Sealed tube; 213 Example 213 2-(8-((3-methyl-4-((1-methyl-1/-/-benzorcnimidazol-5-yl)oxy)phenyl)amino)pyhmidor5,4- dlpyrimidin-2-yl)-2-azaspiror3.31heptan-6-ol A 1-dram vial was charged with A/-(3-methyl-4-((1 -methyl-1 /-/-benzo[c(]imidazol-5- yl)oxy)phenyl)-6-(methylsulfinyl)pyrimido[5,4-c(]pyrimidin-4-amine (25 mg, 56 pmol), 2- azaspiro[3.3]heptan-6-ol hydrochloride (25 mg, 0.17 mmol), diisopropylethylamine (59 mI_, 0.34 mmol), and DMSO (0.56 ml_). The vial was capped and heated to 80 °C for 2.5 hours, upon which the volatiles were removed in vacuo. Purification by column chromatography (Biotage Selekt, RediSep Gold 12G, 1-8% MeOH/CHCh) provided 2-(8-((3-methyl-4-((1-methyl-1H- benzo[c(]imidazol-5-yl)oxy)phenyl)amino)pyrimido[5,4-c(]pyrimidin-2-yl)-2-azaspiro[3.3]heptan-6- ol (24 mg, 45 pmol, 80%, 93% purity) as a foam m/z (APCI-pos) M+1 = 495.3; 1H NMR (400 MHz, CDCh) d 9.00 (s, 1 H), 8.53 (d, J = 3.7 Hz, 2H), 7.84 (s, 1 H), 7.74 (dd, J = 2.8, 0.8 Hz, 1 H), 7.66 (dd, J = 8.6, 2.7 Hz, 1H), 7.33 (dd, J = 8.7, 0.5 Hz, 1 H), 7.29 (dd, J = 2.3, 0.6 Hz, 1 H), 7.07 (dd, J = 8.7, 2.3 Hz, 1 H), 6.94 (d, J = 8.6 Hz, 1H), 4.34 (q, J = 7.1 Hz, 1H), 4.24 (d, J = 5.0 Hz, 4H), 3.85 (s, 3H), 2.67 (ddd, J = 10.0, 6.9, 3.1 Hz, 2H), 2.23 (ddd, J = 10.1, 7.3, 3.1 Hz, 2H), 2.17 (s, 1H), 1.60 (s, 2H).
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 2.5h; Inert atmosphere; Sealed tube; 213 Example 213 2-(8-((3-methyl-4-((1-methyl-1/-/-benzorcnimidazol-5-yl)oxy)phenyl)amino)pyhmidor5,4- dlpyrimidin-2-yl)-2-azaspiror3.31heptan-6-ol A 1-dram vial was charged with A/-(3-methyl-4-((1 -methyl-1 /-/-benzo[c(]imidazol-5- yl)oxy)phenyl)-6-(methylsulfinyl)pyrimido[5,4-c(]pyrimidin-4-amine (25 mg, 56 pmol), 2- azaspiro[3.3]heptan-6-ol hydrochloride (25 mg, 0.17 mmol), diisopropylethylamine (59 mI_, 0.34 mmol), and DMSO (0.56 ml_). The vial was capped and heated to 80 °C for 2.5 hours, upon which the volatiles were removed in vacuo. Purification by column chromatography (Biotage Selekt, RediSep Gold 12G, 1-8% MeOH/CHCh) provided 2-(8-((3-methyl-4-((1-methyl-1H- benzo[c(]imidazol-5-yl)oxy)phenyl)amino)pyrimido[5,4-c(]pyrimidin-2-yl)-2-azaspiro[3.3]heptan-6- ol (24 mg, 45 pmol, 80%, 93% purity) as a foam m/z (APCI-pos) M+1 = 495.3; 1H NMR (400 MHz, CDCh) d 9.00 (s, 1 H), 8.53 (d, J = 3.7 Hz, 2H), 7.84 (s, 1 H), 7.74 (dd, J = 2.8, 0.8 Hz, 1 H), 7.66 (dd, J = 8.6, 2.7 Hz, 1H), 7.33 (dd, J = 8.7, 0.5 Hz, 1 H), 7.29 (dd, J = 2.3, 0.6 Hz, 1 H), 7.07 (dd, J = 8.7, 2.3 Hz, 1 H), 6.94 (d, J = 8.6 Hz, 1H), 4.34 (q, J = 7.1 Hz, 1H), 4.24 (d, J = 5.0 Hz, 4H), 3.85 (s, 3H), 2.67 (ddd, J = 10.0, 6.9, 3.1 Hz, 2H), 2.23 (ddd, J = 10.1, 7.3, 3.1 Hz, 2H), 2.17 (s, 1H), 1.60 (s, 2H).
  • 20
  • [ 1630907-10-6 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride In dichloromethane at 25℃; for 2h; 39.1 Step 5 General procedure: Intermediate 31-4 (100 mg, 142 mmol, 1 equiv) and ethanolamine (86.4 mg, 1.42 mmol, 85.6 ml, 10 equiv) wasdissolved in dichloromethane (3 mL), then sodium triacetoxyborohydride (90.0 mg, 425 mmol, 3 equiv) was added tothe reaction mixture, stirred at 25 °C for 2 hours. After the reaction was completed, water (10 mL) was added to thereaction mixture, the reaction mixture was extracted with dichloromethane (30 mL). The organic phase was washed withsaturated brine (40 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was subjected tosilica gel thin layer chromatography (petroleum ether: ethyl acetate: ethanol=1:3:1) to obtain compound 31-5. MS-ESI calculated value [M+H]+ 751, measured value 751.
  • 21
  • [ 1630907-10-6 ]
  • [ 2639163-48-5 ]
  • [ 2639163-49-6 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; 53.4 Step 4 Intermediate 53-2 (130 mg, 179.87 (mmol) was dissolved in dichloromethane (3 mL), and then intermediate39-1 (40.37 mg, 269.81 mmol, hydrochloride), diisopropylethylamine (427.08 mg, 2.78 mmol) and sodium triacetoxyborohydride(114.37 mg, 539.61 mmol) were added thereto. The reaction was conducted at room temperature for 0.5hours. After the reaction was completed, the reaction was quenched with water (10 mL), diluted with dichloromethane(10 mL), and extracted with dichloromethane (10 mL32). The organic phase was washed with saturated brine (5 mL32),dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was subjected to high performanceliquid chromatography (chromatographic column: Xtimate C18 15025 mm10 microns; mobile phase: mobile phase A:formic acid aqueous solution with volume fraction of 0.225 %; mobile phase B: acetonitrile; B%: 9%-39%, 10 minutes)to obtain intermediate 53-3. MS-ESI calculated value [M+H]+ 821, measured value 821.
  • 22
  • [ 1630907-10-6 ]
  • [ 2639163-54-3 ]
  • [ 2639163-55-4 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine In dichloromethane at 30℃; for 12h; 57.3 Step 3 Intermediates 57-2 (150 mg, 209 mmol, 1 equiv) and 39-1 (46.9 mg, 313 mmol, 85.6 ml, 1.5 equiv, hydrochloride)were dissolved in dichloromethane (3 mL), and then N,N-diisopropylethylamine (81.0 mg, 627 mmol, 109 ml, 3 equiv)and sodium triacetoxyborohydride (133 mg, 627 mmol, 3 equiv) were added to the reaction mixture, stirred at 30 °C for12 hours. After the reaction was completed, water (5 mL) was added, the reaction mixture was extracted with dichloromethane(8 mL33). The organic phase was washed with saturated brine (10 mL32), dried over anhydrous sodiumsulfate, filtered, and concentrated. The concentrated residue was subjected to silica gel thin-layer chromatography(petroleum ether: ethyl acetate: ethanol=4:3:1) to obtain compound 57-3. MS-ESI calculated value [M+H]+ 814, measured value 814.
  • 23
  • [ 1630907-10-6 ]
  • [ CAS Unavailable ]
  • [ 2639163-62-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-azaspiro[3.3]heptan-6-ol hydrochloride; C36H39Cl2F2N5O5Si With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 25℃; for 1.5h; 62.3 Step 3 Compound 62-2 (150 mg, 197.70 mmol, 1 equiv) was dissolved in dichloromethane (2 mL), and then compound39-1 (44.37 mg, 296.56 mmol, 1.5 equiv, hydrochloride) and N,N-diisopropylethylamine (38.33 mg, 296.56 mmol, 51.65ml, 1.5 equiv) were added thereto. The reaction mixture was stirred at 25 °C for 0.5 hours, then sodium triacetoxyborohydride(125.70 mg, 593.11 mmol, 3 equiv) was added, and the reaction was conducted at 25°C for 1.5 hours. After thereaction was completed, the reaction mixture was diluted with water (5 mL), and extracted with ethyl acetate (3 mL33).The combined organic phase was washed with saturated brine (5 mL32), dried over anhydrous sodium sulfate, filteredand concentrated under reduced pressure. The residue was subjected to silica gel thin layer chromatography (petroleumether: ethyl acetate: ethanol=4:3:1) to obtain compound 62-3.MS-ESI calculated value [M+H]+ 855, measured value 855.
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 1630907-10-6 ]

Alcohols

Chemical Structure| 1357923-33-1

[ 1357923-33-1 ]

2-(Azetidin-3-yl)propan-2-ol hydrochloride

Similarity: 0.76

Chemical Structure| 1421033-80-8

[ 1421033-80-8 ]

(S)-2-(Pyrrolidin-3-yl)ethanol hydrochloride

Similarity: 0.75

Chemical Structure| 1185293-84-8

[ 1185293-84-8 ]

3-Methylpiperidin-4-ol hydrochloride

Similarity: 0.73

Chemical Structure| 373603-88-4

[ 373603-88-4 ]

3,3-Dimethylpiperidin-4-ol

Similarity: 0.73

Chemical Structure| 22990-34-7

[ 22990-34-7 ]

2-(4-Piperidyl)-2-propanol

Similarity: 0.70

Related Parent Nucleus of
[ 1630907-10-6 ]

Aliphatic Heterocycles

Chemical Structure| 1357923-33-1

[ 1357923-33-1 ]

2-(Azetidin-3-yl)propan-2-ol hydrochloride

Similarity: 0.76

Chemical Structure| 1421033-80-8

[ 1421033-80-8 ]

(S)-2-(Pyrrolidin-3-yl)ethanol hydrochloride

Similarity: 0.75

Chemical Structure| 1417633-09-0

[ 1417633-09-0 ]

7-Oxa-2-azaspiro[3.5]nonane hydrochloride

Similarity: 0.74

Chemical Structure| 1185293-84-8

[ 1185293-84-8 ]

3-Methylpiperidin-4-ol hydrochloride

Similarity: 0.73

Chemical Structure| 373603-88-4

[ 373603-88-4 ]

3,3-Dimethylpiperidin-4-ol

Similarity: 0.73

Azetidines

Chemical Structure| 1357923-33-1

[ 1357923-33-1 ]

2-(Azetidin-3-yl)propan-2-ol hydrochloride

Similarity: 0.76

Chemical Structure| 1417633-09-0

[ 1417633-09-0 ]

7-Oxa-2-azaspiro[3.5]nonane hydrochloride

Similarity: 0.74

Chemical Structure| 1588441-26-2

[ 1588441-26-2 ]

7-Methyl-2,7-diazaspiro[3.5]nonane dihydrochloride

Similarity: 0.66

Chemical Structure| 1610028-42-6

[ 1610028-42-6 ]

2-Methyl-2,7-diazaspiro[3.5]nonane dihydrochloride

Similarity: 0.66

Chemical Structure| 928038-44-2

[ 928038-44-2 ]

Azetidin-3-ylmethanol hydrochloride

Similarity: 0.61

Spiroes

Chemical Structure| 1417633-09-0

[ 1417633-09-0 ]

7-Oxa-2-azaspiro[3.5]nonane hydrochloride

Similarity: 0.74

Chemical Structure| 1588441-26-2

[ 1588441-26-2 ]

7-Methyl-2,7-diazaspiro[3.5]nonane dihydrochloride

Similarity: 0.66

Chemical Structure| 1610028-42-6

[ 1610028-42-6 ]

2-Methyl-2,7-diazaspiro[3.5]nonane dihydrochloride

Similarity: 0.66

Chemical Structure| 374795-37-6

[ 374795-37-6 ]

2-Oxa-7-azaspiro[4.5]decane hydrochloride

Similarity: 0.63

Chemical Structure| 479195-19-2

[ 479195-19-2 ]

2-Oxa-8-azaspiro[4.5]decane hydrochloride

Similarity: 0.62