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Chemical Structure| 236406-47-6
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Product Details of [ 236406-47-6 ]

CAS No. :236406-47-6 MDL No. :MFCD11656757
Formula : C14H27ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SABRTFCGXPHVTA-UHFFFAOYSA-N
M.W : 290.83 Pubchem ID :67269440
Synonyms :

Safety of [ 236406-47-6 ]

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 [ 236406-47-6 ]

* 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 [ 236406-47-6 ]

[ 236406-47-6 ] Synthesis Path-Downstream   1~61

  • 1
  • [ 236406-47-6 ]
  • [ 81995-32-6 ]
  • C25H40N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; triethylamine; In 1,1-dichloroethane; at 20℃; Example: 7; 3- (2-isobutoxybenzyl)-9- (pyridin-4-ylcarbonyl)-3, 9-diazaspiro [5.5] undecane dihydrochloride; Scheme 1; a) 3- (2-isobutoxybenzyl)-3, 9-diazaspiro [5.5] undecane dihydrochloride; A mixture of tert-butyl 3,9-diazaspiro [5.5] undecane-3-carboxylate hydrochloride (l. Og, 3. 44mmol), 2-isobutoxybenzaldehyde (0.612g, 3. 44mmol), triethylamine (0.718 ml, 5.16 mmol), sodium triacetoxyborohydride (1.02g, 4. 81mmol) and dichloroethane (25ml) was stirred at room temperature overnight. The reaction mixture was concentrated, then partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution. The organic layer was isolated and evaporated to dryness to provide an oil. The oil was dissolved in dichloromethane (25ml), and then trifluoroacetic acid (5ml) was added. After stirring for 3 hours the reaction mixture was concentrated to give an orange oil which was dissolved in ethyl acetate and washed with 1M hydrochloric acid (3x). The combined aqueous layers were concentrated, then azeotroped with toluene, and triturated with diethyl ether to provide the title compound (1.2g, 3.09mmol) as an off-white solid.
  • 2
  • 2-isobutoxynicotinic acid [ No CAS ]
  • [ 236406-47-6 ]
  • [ 851325-48-9 ]
YieldReaction ConditionsOperation in experiment
94% With N-ethyl-N,N-diisopropylamine; HATU; In DMF (N,N-dimethyl-formamide); at 20℃; for 1h; Example : 9; 3- (4-chlorobenzoyl)-9- [ (2-isobutoxypyridin-3-yl) methyl]-3, 9-diazaspiro [5. 5] undecane dihydrochloride; Scheme 1; a) tert-butyl 9-[(2-isobutoxypyridin-3-yl) carbonyl]-3, 9-diazaspiro [5.5] undecane-3- carboxylate; To a solution tert-butyl 3,9-diazaspiro [5.5] undecane-3-carboxylate hydrochloride (293mg, l. 0mmol), 2-isobutoxynicotinic acid (214mg, l. lmmol) and diisopropylethylamine (0.385 p1, 2. 2mmol) in dryN, N-dimethylformamide (9. 5ml) was added 0- (7-azabenzotriazol-1- yl)-N, N, N', N-tetramethyluronium hexafluorophosphate (400mg, 1. 05mmol). After stirring the solution for 1 hour, the reaction mixture was poured onto saturated sodium hydrogen carbonate, and extracted with ethyl acetate (2x). The combined organic layers were washed with water, brine, then dried (Na2S04), and concentrated to a viscous gum. The gum was subjected to silica-gel column chromatography using a mixture of ethyl acetate and cyclohexane (gradient 25: 75 to 70: 30, v/v) as eluent to provide the title compound (403mg, 94%) as a colourless viscous gum.
  • 3
  • [ 236406-47-6 ]
  • [ 39515-51-0 ]
  • [ 912461-44-0 ]
YieldReaction ConditionsOperation in experiment
47% With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; for 15h;Heating / reflux; Intermediate B: 3-[3-phenoxybenzyl]-3,9-diazaspiro[5.5]undecane dihydrochloridea) tert-butgammal 9-(3-phenoxybenzyl)-3,9-diazaspiro [5.5]undecane-3-carboxylate EPO <DP n="23"/>A mixture of ter^-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride (1.0 g, 3.4 mmol), 3-phenoxybenzaldehyde (0.75 g, 3.8 mmol)., triethylamine (0.72 mL, 5.2 mmol), sodium triacetoxyborohydride (1.02 g, 4.8 mmol), dichloroethane (35 mL) and dimethylformarnide (5 mL) was heated at reflux overnight. The reaction mixture was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution. The organic layer was isolated and evaporated to dryness. Column cromatography on SiO2 gave the title compound (0.71 g, 47%).APCI-MS m/z: 437.3 [MH+]
47% With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;Heating / reflux; ) tert-butyl P-CS-phenoxybenzy^-SjP-diazaspirofS.SJundecane-S-carboxylateA mixture offers-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride (1.0 g, 3.4 mmol), 3-phenoxybenzaldehyde (0.75 g, 3.8 mmol), triethylamine (0.72 mL5 5.2 mmol), sodium triacetoxyborohydride (1.02 g, 4.8 mmol), dichloroethane (35 mL) and o dimethylformamide (5 mL) was heated at reflux overnight. The reaction mixture was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution. The organic layer was isolated and evaporated to dryness. Column cromatography on SiO2 gave the title compound (0.71 g, 47%).I5 APCI-MS m/z: 437.3 [MH+]
  • 4
  • [ 236406-47-6 ]
  • [ 62256-40-0 ]
  • [ 912461-47-3 ]
YieldReaction ConditionsOperation in experiment
53% a) tert-butyl Q-fl-Cl-methoxyphenoxy^enzylj-S^-diazaspirofS.Slundecane-S- carboxylatetert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride (1.50 g, 5.2 mmol), 2- (2-methoxyphenoxy)benzaldehyde (1.24 g, 5.4 mmol), triethylamine (1.08 mL, 7.74 mmol) and sodium triacetoxyborohydride (1.23g, 5.8 mmol) was dissolved in dichloromethane (40 mL) and dry DMF (15 mL). The pH was adjusted to 4 with AcOH and the mixture was stirred at room temperature over night. Another batch of sodium triacetoxyborohydride (1.0 g, 4.72 mmol) was added and the mixture was stirred at 40C for 2 hrs. The mixture was diluted with EtOAc (150 mL) and washed with sodium bicarbonate-solution, H2O and brine and dried over Na2SO4 and evaporated. The crude product was purified using column chromatography on SiO2 eluting with Heptane :EtO Ac 4:1 + 2 vol% NEt3 affording 1.27 g (53%) of the title compound as a colourless oil.
53% a) tert-butyl 9- [2-(2-methoxyphenoxy)b enzyl] -3 ,9-diazaspiro [5.5] undecane-3-I5 carboxylatefert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride (1.50 g, 5.2 mmol), 2- (2-methoxyphenoxy)benzaldehyde (1.24 g, 5.4 mmol), triethylamine (1.08 mL, 7.74 mmol) and sodium triacetoxyborohydride (1.23g, 5.8 mmol) was dissolved in 2Q dichloromethane (40 mL) and dry DMF (15 mL). The pH was adjusted to 4 with AcOH and the mixture was stirred at room temperature over night. Another batch of sodium triacetoxyborohydride (1.0 g, 4.72 mmol) was added and the mixture was stirred at 400C for 2 hrs. The mixture was diluted with EtOAc (150 mL) and washed with sodium bicarbonate-solution, H2O and brine and dried over Na2SO4 and evaporated. The crude EPO <DP n="29"/>product was purified using column chromatography on SiO2 eluting with Heptane:EtOAc 4:1 + 2 vol% NEt3 affording 1.27 g (53%) of the title compound as a colourless oil.1H NMR (400 MHz, DMSO-D6) delta 7.42 (dd, J= 7.5, 1.5 Hz, IH), 7.17-7.10 (m, 3H), 7.04 s (td, J= 7.4, 0.9 Hz, IH), 6.95-6.88 (m, 2H), 6.84 (d, J= 7.6 Hz5 IH), 6.58 (d, J= 8.0 Hz, IH), 3.74 (s, 3H), 3.54 (s, 2H)3 3.30-3.23 (m, 6H), 2.40-2.34 (m, 4H), 1.46-1.40 (m, 12H), 1.38 (s, llH), 1.34-1.29 (m, 14H)APCI-MS m/z: 467.3 [MH+]
  • 5
  • [ 236406-47-6 ]
  • [ 66855-92-3 ]
  • [ 912461-49-5 ]
YieldReaction ConditionsOperation in experiment
64% With sodium tris(acetoxy)borohydride; triethylamine; In acetonitrile;Heating / reflux; c) 3-[3-(2-methoxyphenoxy)benzyl]-3,9-diazaspiro[5.5]undecane dihydrochlorideTo a solution of tert-butyl 9-[3-(2-methoxyphenoxy)benzyl]-3,9-diazaspiro[5.5]undecane- 3-carboxylate (1.6 g, 3.4 mmol) in 50 mL of THF was added 7 mL of cone. HCL After 2 h stirring at room temperature the reaction mixture was evaporated and co-evaporated three times with methanol and toluene. The title compound was obtained as a white solid.1H NMR (400 MHz, DMSO-D6) delta 7.37 (t, J= 7.9 Hz, IH)3 7.29 (d, J= 7.7 Hz, IH), 7.26- 7.16 (m, 2H), 7.14 (s, IH), 7.10-7.05 (m, IH), 7.02-6.96 (m, IH), 6.88-6.81 (m, IH), 4.25 (d, J= 5.4 Hz, 2H), 3.73 (s, 3H), 3.13-2.94 (m, 8H), 1.88-1.64 (m, 6H), 1.56-1.47 (m, 2H)APCI-MS m/z: 367.2 [MH+]
64% With sodium tris(acetoxy)borohydride; triethylamine; In acetonitrile;Heating / reflux; b) tert-buty 9-[3-(2-methoxyphenoxy)benzyl]-3,9-diazaspiro[5.5]undecane-3- carboxylate EPO <DP n="31"/>NaB(OAc)3H, CH3CN, TEA,A mixture of <strong>[236406-47-6]tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride</strong> (1.4 g, 5.0 mmol), 3-(2-methoxyphenoxy)benzaldehyde (1.7 g, 7.5mmol, triethylamine (1 mL, 7.5 5 mmol), sodium triacetoxyborohydride (1.6 g, 7.5 mmol) and acetonitrile were heated at reflux overnight. The reaction mixture was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution. The organic layer was isolated and evaporated to dryness. Column cromatography on SiO2 gave the title compound (1.5 g, 64%).io 1H NMR (400 MHz, DMSO-D6) delta 7.26-7.14 (m, 3H), 7.04-6.90 (m, 3H), 6.76 (s, IH), 6.71-6.66 (m, IH), 3.39 (s, 2H), 3.31 (s, 5H), 3.29-3.23 (m, 4H), 2.33-2.25 (m, 4H), 1.43- 1.36 (m, HH), 1.35-1.27 (m, 4H)APCI-MS m/z: 467.3 [MH +]
64% With sodium tris(acetoxy)borohydride; triethylamine; In acetonitrile;Heating / reflux; b) fer-.-butyl 9-[3-(2-methoxyphenoxy)benzyl]-3,9-diazaspiro[5.5]undecane-3- carboxylateA mixture of tert-bntyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride (1.4 g, 5.0 mmol), 3-(2-methoxyphenoxy)benzaldehyde (1.7 g, 7.5mmol, triethylamine (1 mL, 7.5 mmol), sodium triacetoxyborohydride (1.6 g, 7.5 mmol) and acetonitrile were heated at reflux overnight. The reaction mixture was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution. The organic layer was isolated and evaporated to dryness. Column cromatography on SiO2 gave the title compound (1.5 g, 64%).1H NMR (400 MHz, DMSO-D6) delta 7.26-7.14 (m, 3H), 7.04-6.90 (m, 3H), 6.76 (s, IH), 6.71-6.66 (m, IH), 3.39 (s, 2H), 3.31 (s, 5H), 3.29-3.23 (m, 4H), 2.33-2.25 (m, 4H), 1.43- 1.36 (m, HH), 1.35-1.27 (m, 4H) EPO <DP n="27"/>APCI-MS m/z: 467.3 [MH +]
  • 6
  • [ 223575-87-9 ]
  • [ 236406-47-6 ]
  • [ 912461-47-3 ]
YieldReaction ConditionsOperation in experiment
53% a) fer^-butyl 9-[2-(2-methoxyphenoxy)benzyl]-3,9-diazaspiro[5.5]undecane-3- carboxylatetert-ntyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride (1.5 g, 5.2 mmol), 2- (2-methoxyphenoxy)benzaldehyde (1.24 g, 5.4 mmol), trietbylamine (1.08 mL, 7.74 mmol) and sodium triacetoxyborohydride (1.23 g, 5.8 mmol) was dissolved in dichloromethane (40 mL) and dry DMF (15 mL). The pH was adjusted to 4 with AcOH and the mixture was stirred at room temperature over night. Another batch of sodium triacetoxyborohydride (1.0 g, 4.72 mmol) was added and the mixture was stirred at 400C for 2 hrs. The mixture was diluted with EtOAc (150 mL) and washed with sodium bicarbonate-solution, H2O and brine and dried over Na2SO4 and evaporated. The crude product was purified using column chromatography on SiO2 eluting with Heptane:EtOAc 4:1 + 2 vol% NEt3 affording 1.27 g (53%) of the title compound as a colourless oil.1HNMR (400 MHz, DMSO-D6) delta 7.42 (dd, J= 7.5, 1.5 Hz, IH), 7.17-7.10 (m, 3H), 7.04 (td, J= IA, 0.9 Hz, IH), 6.95-6.88 (m, 2H), 6.84 (d, J= 7.6 Hz, IH), 6.58 (d, J= 8.0 Hz, IH), 3.74 (s, 3H), 3.54 (s, 2H), 3.30-3.23 (m, 6H), 2.40-2.34 (m, 4H), 1.46-1.40 (m, 12H), 0 1.38 (s, HH), 1.34-1.29 (m, 14H)APCI-MS m/z: 467.3 [MH+]
  • 7
  • [ 236406-47-6 ]
  • [ 19434-34-5 ]
  • [ 912464-68-7 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 24h; a) t°rMmty^-^-phenoxybenzyty-S^-diazaspirotS^undecane-theta-carboxylate tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride (0.95 g, 3.26 mmol), 2-phenoxybenzaldehyde (0.70 g, 3.54 mmol) and sodium triacetoxyborohydride (0.97 g, 4.56 mmol) were stirred in a mixture Of CH2Cl2 (20 mL), DMF (LO mL) and Et3N (0.68 mL) for 24h at room temperature. Na2CO3 (aq.sat) (30 mL) was added to the reaction mixture. The product was extracted with CH2Cl2, washed with water, dried and the solvent was evaporated. Column cromatography on SiO2 with heptane/EtOAc 1:1 with 2% Et3N gave the title compound (384 mg).1H NMR (400 MHz, CDC13): delta 7.52 (m, IH), 7.29 (m, 3H), 7.14 (m,lH), 7.06 (m, IH), 6.91 (m, 3H), 3.59 (m, 2H), 3.35 (m, 4H), 1.45 (s, 9H), 1.69-1.32 (m, 4H)
  • 8
  • [ 236406-47-6 ]
  • [ 38002-88-9 ]
  • tert-butyl 9-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; In acetonitrile; at 20℃; for 3h; Intermediate A 3-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9-diazaspiro[5.5]undecaneA mixture of tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloric acid salt (5.00 g, 17.2 mmol), 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carbaldehyde (3.26 g, 18.5 mmol), sodium triacetoxyborohydride (5.97 g, 28.2 mmol) and acetonitrile was stirred at room temperature for 3 h. The reaction mixture was applied to silica and eluted first with 20% EtOAc in heptane, and then with EtOAc/MeOH/triethylamine (90/5/5). The fraction containing the crude product was evaporated and to this Intermediate ter/-butyl 9-[(2,2- dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9-diazaspiro[5.5]undecane-3- carboxylate was added IM methanolic hydrochloric acid (50ml) and the mixture was stirred at room temperature for 1 h then evaporated. The residue was purified by acidic ion- sxchange resin to yield the product as a off-white solid (4.71 g, 71%). EPO <DP n="66"/>1HNMR (399.989 MHz, D2O) delta 7.12 (d, IH), 7.01 (d, IH), 6.80 (t, IH), 3.63-3.56 (m, 2H), 3.08-2.99 (m, 4H), 2.95 (s, 2H), 2.66-2.50 (m, 4H), 1.68-1.42 (m, 8H), 1.39-1.30 (m, 6H)APCI-MS m/z: 315.3 [MH+]HPLC (Method A) Retention time: 4.23 minHPLC (Method B) Retention time: 8.07 min
  • 9
  • [ 236406-47-6 ]
  • [ 88-65-3 ]
  • [ 929302-23-8 ]
YieldReaction ConditionsOperation in experiment
92% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃; a) tert-butyl 9-(2-bromobenzoyl)-3,9-diazaspiro[5.5]undecane-3-carboxylate <strong>[236406-47-6]tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride</strong> (1.0 g, 3.44 mmol), 2- bromobenzoic acid (0.83 g, 4.13 mmol), HBTU (1.57 g, 4.13 mmol) and triethylamine (1.44 ml, 10.3 mmol) were dissolved in dichloromethane (20 ml) and stirred at room temperature over night. The mixture was disluted with dichloromethane and washed with aqueous NaHCO3 (sat.). The organic layer was dried over Na2SO4 and evaporated. The residue was purified using column chromatography on SiO2 eluting with Heptane :EtO Ac 10:1 to 1:2 affording 1.38g (92%) of the title compound as a colourless oil. 1H NMR (299.944 MHz, CDC13) delta 7.61 - 7.55 (m, IH), 7.39 - 7.32 (m, IH), 7.27 - 7.21 (m, 2H), 3.86 - 3.72 (m, 2H), 3.47 - 3.31 (m, 4H), 3.31 - 3.10 (m, 2H), 1.71 - 1.33 (m, 17H)
  • 10
  • [ 929302-01-2 ]
  • [ 236406-47-6 ]
YieldReaction ConditionsOperation in experiment
Preparation of compound 3,9-Diaza-spiro[5.5]undecane-3-carboxylic acid tert-butyl esterA mixture of compound 2 (3 g) and Pd(OH)2 (300 mg) in 15 mL of MeOH was stirred under 55 psi of H2 at 35 C overnight. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in anhydrous ether, then HCl(g)/MeOH was added to pH = 6-7. The mixture was filtered to afford compound 3,9-diaza-spiro[5.5]undecane-3- carboxylic acid tert-butyl ester (2.2 g). 1H NMR (CDCl3, HCl salt) delta: 9.49 (br, 2 H), 3.39 - 3.36 (m, 4 H), 3.16 (br, 4 H), 1.82 - 1.79 (m, 4 H), 1.51 - 1.48 (m, 4 H), 1.44 (9 H).
Step G: tert-butyl 3,9-diazaspiror5.5"|undecane-3-carboxylate: A mixture of tert-butyl 9-benzyl- 3,9-diazaspiro[5.5]undecane-3-carboxylate (240 g, 0.7 mol) and Pd(OH)2/C (24 g) in methanol (1.5 L) under hydrogen atmosphere (60 psi) was stirred at 40 C for 24h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was treated with IN HCl/methanol and filtered to afford compound the title compound as a HC1 salt.
  • 11
  • [ 236406-47-6 ]
  • (R)-5-(1-hydroxy-2-(3,9-diazaspiro[5.5]undecan-3-yl)ethyl)-4-methylisobenzofuran-1(3H)-one [ No CAS ]
  • 12
  • [ 236406-47-6 ]
  • 3-methyl-4-(3,9-diazaspiro[5.5]undecan-3-yl)furan-2(5H)-one [ No CAS ]
  • 13
  • [ 236406-47-6 ]
  • 3-fluoro-4-(3,9-diazaspiro[5.5]undecan-3-yl)furan-2(5H)-one [ No CAS ]
  • 14
  • [ 236406-47-6 ]
  • tert-butyl 9-(4-cyclopropyl-5-oxo-2,5-dihydrofuran-3-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
  • 15
  • [ 236406-47-6 ]
  • 3-phenyl-4-(3,9-diazaspiro[5.5]undecan-3-yl)furan-2(5H)-one [ No CAS ]
  • 16
  • [ 236406-47-6 ]
  • tert-butyl 9-(5-oxo-4-phenyl-2,5-dihydrofuran-3-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
  • 17
  • [ 236406-47-6 ]
  • 3-(3,9-diazaspiro[5.5]undecan-3-yl)cyclopent-2-enone [ No CAS ]
  • 18
  • [ 236406-47-6 ]
  • 2-methyl-3-(3,9-diazaspiro[5.5]undecan-3-yl)cyclopent-2-enone [ No CAS ]
  • 19
  • [ 236406-47-6 ]
  • (R)-5-(1-hydroxy-2-(9-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-3,9-diazaspiro[5.5]undecan-3-yl)ethyl)-4-methylisobenzofuran-1(3H)-one [ No CAS ]
  • 20
  • [ 236406-47-6 ]
  • 5-((1R)-2-(9-(2-ethoxy-5-oxo-2,5-dihydrofuran-3-yl)-3,9-diazaspiro[5.5]undecan-3-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one [ No CAS ]
  • 21
  • [ 516-09-6 ]
  • [ 236406-47-6 ]
  • tert-butyl 9-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In isopropyl alcohol; at 108℃; Step A: fe/t-butyl 9-(4-methyl-5-oxo-2.5-dihydrofuran-3-yl)-3.9-diazaspiror5.51undecane-3- carboxylate: A solution of tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate (INTERMEDIATE 26; 397 mg, 1.262 mmol), acetic acid (0.072 mL, 1.262 mmol), and 4- hydroxy-3-methylfuran-2(5H)-one (INTERMEDIATE 30; 160 mg, 1.402 mmol) in 2-propanol (4.14 ml) was heated at 108 C overnight. After concentration the residue was purified on silica gel using EtOAc/hexane as eluting solvents to give tert-butyl 9-(4-methyl-5-oxo-2,5- dihydrofuran-3 -yl)-3 ,9-diazaspiro [5.5]undecane-3 -carboxylate.
  • 22
  • [ 236406-47-6 ]
  • [ 75966-09-5 ]
  • 3-methyl-4-(3,9-diazaspiro[5.5]undecan-3-yl)cyclobut-3-ene-1,2-dione hydrochloride [ No CAS ]
  • 23
  • [ 236406-47-6 ]
  • [ 75966-09-5 ]
  • tert-butyl 9-(2-methyl-3,4-dioxocyclobut-1-en-1-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 25℃; for 4h; Step A: tert-butyl 9-(2-methyl-3,4-dioxocyclobut-1-en-1-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate: The mixture of 3-ethoxy-4-methylcyclobut-3-ene-l, 2-dione (INTERMEDIATE 33; 1.40 g, 10.0 mmol), <strong>[236406-47-6]tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride</strong> (1.16 g, 4.00 mmol) and NEt3 (1.38 mL, 10.0 mmol) in THF (40 mL) was stirred at 25 C for 4 hours. The mixture was concentrated and the residue was purified via BIOTAGE (Uppsala, Sweden) column (EtOAc in DCM: 0 to 40 %) to afford the title compound.
  • 24
  • [ 236406-47-6 ]
  • [ 1548291-89-9 ]
  • tert-butyl 9-(4-fluoro-5-oxo-2,5-dihydrofuran-3-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; palladium diacetate; johnphos; In tetrahydrofuran; at 80℃; Step D: fe/t-butyl 9-(4-fluoro-5-oxo-2,5-dihydrofuran-3-yl)-3,9-diazaspiror5.51undecane-3- carboxylate: The mixture of tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate (INTERMEDIATE 26; 173 mg, 0.680 mmol), 4-fluoro-2-methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate (170mg, 0.680mmol), potassium phosphate (202 mg, 0.952 mmol), 2- (di-tert-butylphosphino)biphenyl (20.28 mg, 0.068 mmol), and Palladium (II) acetate (7.63 mg, 0.034 mmol) in tetrahydrofuran (10 ml) was heated at 80 C for overnight. After filtration through CELITE, the filtrate was concentrated and the residue was purified on silica gel using EtOAc /hexane as eluting solvents to give tert-butyl 9-(4-fluoro-5-oxo-2,5-dihydrofuran-3-yl)- 3,9-diazaspiro[5.5]undecane-3-carboxylate.
  • 25
  • [ 236406-47-6 ]
  • [ 149418-41-7 ]
  • tert-butyl 9-(4-bromo-5-oxo-2,5-dihydrofuran-3-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 40℃; Step A: tert-Bu yl 9-(4-bromo-5-oxo-2.5-dihydrofuran-3-yl)-3.9-diazaspiror5.51undecane-3- carboxylate: tert-Butyl 3, 9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride (500mg, 1.72 mmol) was mixed with DIEA (0.661 mL, 3.78 mmol) in THF (8 mL). 3,4-Dibromofuran-2(5H)- one (457 mg, 1.891 mmol) was added. The mixture was stirred at 40 C overnight. Solvent was then removed with a ROTA VAPOR evaporator and the resulting residue was purified with flash chromatography eluting with 0-10% MeOH/DCM on 40 g silica gel columnto give the title product.
  • 26
  • [ 36904-76-4 ]
  • [ 236406-47-6 ]
  • 5-methyl-4-(3,9-diazaspiro[5.5]undecan-3-yl)furan-2(5H)-one hydrochloride [ No CAS ]
  • 27
  • [ 36904-76-4 ]
  • [ 236406-47-6 ]
  • tert-butyl 9-(2-methyl-5-oxo-2,5-dihydrofuran-3-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In isopropyl alcohol; at 108℃; Step C: tert-butyl 9-(2-methyl-5-oxo-2,5-dihvdrofuran-3-yl)-3,9-diazaspiror5.51undecane-3- carboxylate: The solution of tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate (INTERMEDITE 26; 200 mg, 0.636 mmol), 4-hydroxy-5-methylfuran-2(5H)-one (80 mg, 0.700 mmol) and acetic acid (0.036 mL, 0.636 mmol) in 2-Propanol (4.14 ml) was heated at 108 C overnight. After concentration the residue was purified on reverse phase HPLC using 20-80% acetonitrile (0.1%TFA) to give tert-butyl 9-(2-methyl-5-oxo-2,5-dihydrofuran-3-yl)-3,9- diazaspiro [5.5 ]undecane-3 -carboxylate.
  • 28
  • [ 3859-41-4 ]
  • [ 236406-47-6 ]
  • tert-butyl 9-(3-oxocyclopent-1-en-1-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; at 120℃; for 16h;Sealed tube; Step A: tert-butyl 9-(3-oxocyclopent-1-en-1-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate: To a solution of tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate (INTERMEDIATE 26; 230 mg, 0.904 mmol) in a microwave tube was added 2-propanol (7 ml) followed by cyclopentadione (1 15 mg, 1.175 mmol). The tube was sealed and heated at 120C for 16 hrs. The reaction was concentrated, diluted with ethyl acetate, and washed with saturated NaHC03 (lx). Organic layer was dried over Na2S04, filtered and concentrated to yield tert-butyl 9-(3- oxocyclopent- 1 -en- 1 -yl)-3 ,9-diazaspiro[5.5 ]undecane-3 -carboxylate.
  • 29
  • [ 765-69-5 ]
  • [ 236406-47-6 ]
  • tert-butyl 9-(2-methyl-3-oxocyclopent-1-en-1-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; at 120℃; for 16h;Sealed tube; Step A: tert-butyl 9-(2-methyl-3-oxocyclopent-1-en-1-yl)-3,9-diazaspiro [5.5]undecane-3-carboxylate: To a solution of tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate (INTERMEDIATE 26; 119mg, 0.468 mmol) in a microwave tube was added 2-propanol (7 ml) followed by 2-methyl-l,3-cyclopentadione (62.9 mg, 0.561 mmol). The tube was sealed and heated at 120C for 16 hr. The reaction was concentrated, diluted with ethyl acetate, and washed with saturated NaHC03 (lx). Organic layer was dried overNa2S04, filtered and concentrated to yield tert-butyl 9-(2-methyl-3-oxocyclopent-l-en-l-yl)-3,9-diazaspiro [5.5] undecane -3 -carboxylate.
  • 30
  • [ 236406-47-6 ]
  • [ 1255206-70-2 ]
  • (R)-tert-butyl 9-(2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step A: ( R)-ter t-butyl 9-(2-hvdroxy-2-(4-methyl-l-oxo-l ,3-dihvdroisobenzofuran-5-yl ethyl - 3,9-diazaspiror5.51undecane-3-carboxylate: To a solution of tert-butyl 3,9- diazaspiro[5.5]undecane-3-carboxylate hydrochloride (1 14 g, 0.39 mol) in ethanol (1 L) was added EtsN (60 mL). The mixture was stirred for 2 hours. Then (R)-4-methyl-5-(oxiran-2- yl)isobenzofuran-l(3H)-one (INTERMEDIATE 4B; 75 g, 0.39 mol) was added. The mixture was heated to reflux for 24h. The mixture was concentrated, washed with brine, dried over Na2S04 and concentrated to provide the crude product. The crude product was purified by SFC separation to provide the title compound.
  • 31
  • [ 160133-32-4 ]
  • [ 236406-47-6 ]
  • 32
  • [ 1051383-60-8 ]
  • [ 236406-47-6 ]
  • 33
  • [ 24424-99-5 ]
  • [ 236406-47-6 ]
  • 34
  • 1-t-Butoxycarbonylpiperidine-4,4-diethanol [ No CAS ]
  • [ 236406-47-6 ]
  • 35
  • [ 170228-79-2 ]
  • [ 236406-47-6 ]
  • 36
  • [ 236406-47-6 ]
  • 4-bromo-2-((2-(trimethylsilyl)ethyl)sulfonyl)nicotinonitrile [ No CAS ]
  • [ 824-94-2 ]
  • tert-butyl 9-(3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
  • tert-butyl 9-(3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
The mixture of <strong>[236406-47-6]tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride</strong> (29.3 mg, 0.101 mmol), 4-Bromo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5- yl)pyridine-2-sulfonamide and 4-Bromo-3 -( 1 -(4-methoxybenzyl)- lH-tetrazol-5-yl)pyridine-2- sulfonamide (33 mg, 0.078 mmol), and K2C03 (42.9 mg, 0.310 mmol) in DMF (1 mL) was heated at 140C overnight. The mixture was partitioned between EtOAc (50 mL) and sat. NaHCCh, the organic phase was washed with NaHCCh twice, dried over a2S04, concentrated and the residue was purified on preparative TLC (1000MU) using 10%MeOH/DCM as developing solvents to give the residue which was then further purified on preparative TLC (1000MU) using EtOAc as developing solvent to the title compound.
  • 37
  • [ 236406-47-6 ]
  • 4-bromo-2-((2-(trimethylsilyl)ethyl)sulfonyl)nicotinonitrile [ No CAS ]
  • 4-(3,9-diazaspiro[5.5]undecan-3-yl)-3-(2H-tetrazol-5-yl)pyridine-2-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
To the solution of tert-butyl 9-(3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-2- sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate and tert-butyl 9-(3-(l-(4- methoxybenzyl)-lH-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3- carboxylate (37 mg, 0.062 mmol) in CH2CI2 (2 mL) was added TFA (2 mL, 26.0 mmol), and the resulting solution was stirred at rt for 1 hr, and then was concentrated; to the resulting residue was added triisopropylsilane (98 mg, 0.62 mmol) and TFA (2 mL, 26.0 mmol). The solution was then transfered to a sealed tube and heated at 80C for 1 hr. After removing the volatiles, the residue was dissolved in acetonitrile/water and purified by reverse phase HPLC using 5-40% acetonitrile (0.1%formic acid) over 10 min to give the title compound. LC/MS [M+H]+ 379.
  • 38
  • [ 236406-47-6 ]
  • C11H16BrN5O2SSi [ No CAS ]
  • [ 824-94-2 ]
  • tert-butyl 9-(3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
  • tert-butyl 9-(3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
The solvent was removed, and the dark residue was dissolved in acetonitrile (50 mL). To the solution was added Hunig's base (2.9 g, 22 mmol) and 1-(chloromethyl)-4-methoxybenzene (2.3 g, 14.4 mmol). The mixture was allowed to stir for 72 hours. LC showed a complete reaction. The reaction was diluted with EtOAc, washed with water, and the separated organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting dark residue was loaded onto an 80G ISCO column, and purified by MPLC with hexane and EtOAc. LC/MS [M+H]+: 512. Step E: 4-Bromo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)pyridine-2-sulfonamide and 4-bromo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)pyridine-2-sulfonamide (0300) To a solution of a mixture of 4-bromo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-2-((2-(trimethylsilyl)ethyl)sulfonyl)pyridine and 4-bromo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)pyridine-2-sulfonamide (2.5 g, 4.9 mmol) in THF (10 mL) was added TBAF (20 mL, 20 mmol), and the mixture was allowed to stir at 50 C. for 16 hours. LC showed disappearance of all starting material. The reaction was cooled, and to the reaction was added sodium acetate (4.0 g, 49 mmol) in 10 mL water and (aminooxy)sulfonic acid (5.5 g, 49 mmol). The mixture was allowed to stir at RT for 24 hours. LC showed a good reaction. It was diluted with water, extracted with DCM twice. The extractions were combined, dried over sodium sulfate, and concentrated. The residue was loaded onto a 80G silica column, and purified by MPLC with DCM and MeOH system to afford a mixture of 4-bromo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)pyridine-2-sulfonamide and 4-bromo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)pyridine-2-sulfonamide. LC/MS [M+H]+: 427 Step A: tert-butyl 9-(3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate and tert-butyl 9-(3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate (0676) The mixture of <strong>[236406-47-6]tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride</strong> (29.3 mg, 0.101 mmol), 4-Bromo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)pyridine-2-sulfonamide and 4-Bromo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)pyridine-2-sulfonamide (33 mg, 0.078 mmol), and K2CO3 (42.9 mg, 0.310 mmol) in DMF (1 mL) was heated at 140 C. overnight. The mixture was partitioned between EtOAc (50 mL) and sat. NaHCO3, the organic phase was washed with NaHCO3 twice, dried over Na2SO4, concentrated and the residue was purified on preparative TLC (1000MU) using 10% MeOH/DCM as developing solvents to give the residue which was then further purified on preparative TLC (1000MU) using EtOAc as developing solvent to the title compound
  • 39
  • [ 236406-47-6 ]
  • C11H16BrN5O2SSi [ No CAS ]
  • 4-(3,9-diazaspiro[5.5]undecan-3-yl)-3-(2H-tetrazol-5-yl)pyridine-2-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
The solvent was removed, and the dark residue was dissolved in acetonitrile (50 mL). To the solution was added Hunig's base (2.9 g, 22 mmol) and 1-(chloromethyl)-4-methoxybenzene (2.3 g, 14.4 mmol). The mixture was allowed to stir for 72 hours. LC showed a complete reaction. The reaction was diluted with EtOAc, washed with water, and the separated organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting dark residue was loaded onto an 80G ISCO column, and purified by MPLC with hexane and EtOAc. LC/MS [M+H]+: 512. Step E: 4-Bromo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)pyridine-2-sulfonamide and 4-bromo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)pyridine-2-sulfonamide (0300) To a solution of a mixture of 4-bromo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-2-((2-(trimethylsilyl)ethyl)sulfonyl)pyridine and 4-bromo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)pyridine-2-sulfonamide (2.5 g, 4.9 mmol) in THF (10 mL) was added TBAF (20 mL, 20 mmol), and the mixture was allowed to stir at 50 C. for 16 hours. LC showed disappearance of all starting material. The reaction was cooled, and to the reaction was added sodium acetate (4.0 g, 49 mmol) in 10 mL water and (aminooxy)sulfonic acid (5.5 g, 49 mmol). The mixture was allowed to stir at RT for 24 hours. LC showed a good reaction. It was diluted with water, extracted with DCM twice. The extractions were combined, dried over sodium sulfate, and concentrated. The residue was loaded onto a 80G silica column, and purified by MPLC with DCM and MeOH system to afford a mixture of 4-bromo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)pyridine-2-sulfonamide and 4-bromo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)pyridine-2-sulfonamide. LC/MS [M+H]+: 427 Step A: tert-butyl 9-(3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate and tert-butyl 9-(3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate (0676) The mixture of <strong>[236406-47-6]tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride</strong> (29.3 mg, 0.101 mmol), 4-Bromo-3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)pyridine-2-sulfonamide and 4-Bromo-3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)pyridine-2-sulfonamide (33 mg, 0.078 mmol), and K2CO3 (42.9 mg, 0.310 mmol) in DMF (1 mL) was heated at 140 C. overnight. The mixture was partitioned between EtOAc (50 mL) and sat. NaHCO3, the organic phase was washed with NaHCO3 twice, dried over Na2SO4, concentrated and the residue was purified on preparative TLC (1000MU) using 10% MeOH/DCM as developing solvents to give the residue which was then further purified on preparative TLC (1000MU) using EtOAc as developing solvent to the title compound Step B: 4-(3,9-diazaspiro[5.5]undecan-3-yl)-3-(2H-tetrazol-5-yl)pyridine-2-sulfonamide (0677) To the solution of tert-butyl 9-(3-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate and tert-butyl 9-(3-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-2-sulfamoylpyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate (37 mg, 0.062 mmol) in CH2Cl2 (2 mL) was added TFA (2 mL, 26.0 mmol), and the resulting solution was stirred at rt for 1 hr, and then was concentrated; to the resulting residue was added triisopropylsilane (98 mg, 0.62 mmol) and TFA (2 mL, 26.0 mmol). The solution was then transferred to a sealed tube and heated at 80 C. for 1 hr. After removing the volatiles, the residue was dissolved in acetonitrile/water and purified by reverse phase HPLC using 5-40% acetonitrile (0.1% formic acid) over 10 min to give the title compound. LC/MS [M+H]+ 379.
  • 40
  • [ 236406-47-6 ]
  • [ 70258-18-3 ]
  • tert-butyl 9-((6-chloropyridin-3-yl)methyl)-3,9-diazaspiro[5.5]undecan-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate; In acetonitrile; at 70℃; for 16h; <strong>[236406-47-6]tert-butyl 3,9-diazaspiro[5.5]undecan-3-carboxylate hydrochloride</strong>(400mg, 1.38mmol)and 2-chloro-5-(chloromethyl)pyridine(224 mg, 1.38 mmol) was dissolved in acetonitrile (50 mL), potassium carbonate (952 mg, 6.9 mmol) was added and reacted at 70 C for 16 hours.The organic phase was combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo The title compound was obtained as a pale yellow oil (450 mg, yield 86%).
  • 41
  • [ 236406-47-6 ]
  • 3-((6-chloropyridin-3-yl)methyl)-3,9-diazaspiro[5.5]undecane [ No CAS ]
  • 42
  • [ 236406-47-6 ]
  • 3-((6-chloropyridin-3-yl)methyl)-9-methyl-3,9-diazaspiro[5.5]undecane [ No CAS ]
  • 43
  • [ 236406-47-6 ]
  • 5-fluoro-4-(4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole-6-yl)-N-(5-((9-methyl-3,9-diazaspiro[5.5]undecane-3-yl)methyl)pyridine-2-yl)pyridine-2-amine [ No CAS ]
  • 44
  • [ 236406-47-6 ]
  • 3-[2-(2-methoxyphenoxy)benzyl]-9-(1-oxidoisonicotinoyl)-3,9-diazaspiro[5.5]undecane [ No CAS ]
  • 45
  • [ 236406-47-6 ]
  • 3-[(1-oxidopyridin-2-yl)carbonyl]-9-(3-phenoxybenzyl)-3,9-diazaspiro[5.5]undecane bis(trifluoroacetate) [ No CAS ]
  • 46
  • [ 236406-47-6 ]
  • 3-[3-phenoxybenzyl]-3,9-diazaspiro[5.5]undecane dihydrochloride [ No CAS ]
  • 47
  • [ 236406-47-6 ]
  • 3-[2-(2-methoxyphenoxy)benzyl]-3,9-diazaspiro[5.5]undecane dihydrochloride [ No CAS ]
  • 48
  • [ 236406-47-6 ]
  • (2-[9-(2-phenoxybenzyl)-3,9-diazaspiro[5.5]undec-3-yl]carbonyl}phenyl)acetic acid [ No CAS ]
  • 49
  • [ 236406-47-6 ]
  • 4,5-dichloro-2-({9-[2-(2-methoxyphenoxy)benzyl]-3,9-diazaspiro[5.5]undec-3-yl}carbonyl)benzoic acid [ No CAS ]
  • 50
  • [ 236406-47-6 ]
  • C32H36N2O4 [ No CAS ]
  • 51
  • [ 236406-47-6 ]
  • 3-(2-phenoxybenzyl)-3,9-diazaspiro[5.5]undecane dihydrochloride [ No CAS ]
  • 52
  • [ 236406-47-6 ]
  • [ 39515-51-0 ]
  • 3-[3-phenoxybenzyl]-3,9-diazaspiro[5.5]undecane dihydrochloride [ No CAS ]
  • 53
  • [ 236406-47-6 ]
  • 5-({9-[2-(2-methoxyphenoxy)benzyl]-3,9-diazaspiro[5.5]undec-3-yl}carbonyl)-6-(trifluoromethyl)pyridin-2(1H)-one trifluoroacetate [ No CAS ]
  • 54
  • [ 236406-47-6 ]
  • [ 96-32-2 ]
  • tert-butyl 9-(2-methoxy-2-oxoethyl)-3,9-diazaspiro[5.5]undecane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate; In acetonitrile; at 85℃; for 3h;Inert atmosphere; Intermediate 43a: tert-Butyl 9-(2-methoxy-2-oxoethyl)-3,9-diazaspiro[5.5]undecane-3-carboxylate Methyl 2-bromoacetate (0.406 mL, 4.29 mmol) was added to potassium carbonate (3.95 g, 28.61 mmol) and <strong>[236406-47-6]tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate hydrochloride</strong> (1.04 g, 3.58 mmol) in acetonitrile (12 mL) at 20 C. under nitrogen. The resulting suspension was stirred at 85 C. for 3 hours. The reaction mixture was diluted with EtOAc (75 mL), and washed sequentially with water (10 mL), saturated NaHCO3 (10 mL), and saturated brine (5 mL). The organic layer was dried with MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 5% 1M NH3/MeOH in dichloromethane. Pure fractions were evaporated to dryness to afford the title compound (1.163 g, 100%) as a colourless oil; 1H NMR (400 MHz, DMSO-d6, 30 C.) 1.30-1.37 (4H, m), 1.39 (9H, s), 1.40-1.47 (4H, m), 2.4-2.49 (4H, m), 3.21 (2H, s), 3.24-3.30 (4H, m), 3.61 (3H, s).
  • 55
  • [ 236406-47-6 ]
  • methyl 2-(3,9-diazaspiro[5.5]undecan-3-yl)acetate [ No CAS ]
  • 56
  • [ 236406-47-6 ]
  • methyl 2-(9-(2-(3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenoxy)ethyl)-3,9-diazaspiro[5.5]undecan-3-yl)acetate [ No CAS ]
  • 57
  • [ 236406-47-6 ]
  • 2-(9-(2-(3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenoxy)ethyl)-3,9-diazaspiro[5.5]undecan-3-yl)acetic acid [ No CAS ]
  • 58
  • [ 236406-47-6 ]
  • (2S,4R)-1-((S)-2-(2-(9-(2-(3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenoxy)ethyl)-3,9-diazaspiro[5.5]undecan-3-yl)acetamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide [ No CAS ]
  • 59
  • [ 236406-47-6 ]
  • methyl 2-(9-(2-(3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenoxy)acetyl)-3,9-diazaspiro[5.5]undecan-3-yl)acetate [ No CAS ]
  • 60
  • [ 236406-47-6 ]
  • 2-(9-(2-(3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenoxy)acetyl)-3,9-diazaspiro[5.5]undecan-3-yl)acetic acid [ No CAS ]
  • 61
  • [ 236406-47-6 ]
  • (2S,4R)-1-((S)-2-(2-(9-(2-(3,5-difluoro-4-((1R,3R)-2-(2-fluoro-2-methylpropyl)-3-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenoxy)acetyl)-3,9-diazaspiro[5.5]undecan-3-yl)acetamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide [ No CAS ]
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