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[ CAS No. 161511-85-9 ] {[proInfo.proName]}

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Chemical Structure| 161511-85-9
Chemical Structure| 161511-85-9
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Product Details of [ 161511-85-9 ]

CAS No. :161511-85-9 MDL No. :MFCD03093620
Formula : C9H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :XIRUXUKRGUFEKC-ZETCQYMHSA-N
M.W : 187.24 Pubchem ID :10511797
Synonyms :

Calculated chemistry of [ 161511-85-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.95
TPSA : 49.77 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
Log Po/w (XLOGP3) : 0.62
Log Po/w (WLOGP) : 0.61
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 0.36
Consensus Log Po/w : 0.91

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.13
Solubility : 14.0 mg/ml ; 0.0746 mol/l
Class : Very soluble
Log S (Ali) : -1.24
Solubility : 10.8 mg/ml ; 0.0576 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.55
Solubility : 53.1 mg/ml ; 0.284 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.6

Safety of [ 161511-85-9 ]

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 [ 161511-85-9 ]

* 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 [ 161511-85-9 ]

[ 161511-85-9 ] Synthesis Path-Downstream   1~19

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YieldReaction ConditionsOperation in experiment
100% Example 16 (S)-tert-Butyl 2-(Hydroxymethyl)azetidine-1-carboxylate (14).17 To a solution of 13 (0.94 g, 4.7 mmol) in THF (10 mL) was added slowly a 1 M BH3 in THF (21.0 mL) at 0 C. The mixture was stirred 2 days at ambient temperature, then cold water (20 mL) was added at 0 C. After evaporation of the THF in vacuo, an 10% aqueous solution of citric acid (15 mL) was added and extracted with ethyl acetate (50 mL*2). The combined ethyl acetate was washed with saturated NaHCO3 (30 mL) and NaCl (30 mL), and dried over Na2SO4. Evaporation of the ethyl acetate in vacuo afforded 0.86 g (100%) of 14 as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 4.40 (m, 1), 3.85-3.70 (m, 3H), 2.13 (m, 1H), 1.90 (m, 1H), 1.42 (s, 9H).
87% With boron dimethyl-trifluoro sulphide; In tetrahydrofuran; at 0℃; for 2h;Heating / reflux; (S)-1-(tert-butoxycarbonyl)-2-azetidinecarboxylic acid (10.42 g, 49.4mmol) was introduced into a 500-mLpear-shaped flask, and tetrahydrofuran (200 mL) was added to dissolve the compound. Then, a tetrahydrofuran solution of 10 M borane-dimethyl sulfide complex salt (9.87 mL, 98.7 mmol) was slowly added at 0C, and the mixture was heated to reflux for 2 hours while stirring. The reaction solution was left to cool, and then was concentrated under reduced pressure. Ice water (100 mL) was poured thereto, and the mixture was extracted with ethyl acetate (200 mLx2). The extract was washed with saturated brine (200 mL), and then dried over anhydrous sodium sulfate. After filtering the extract, the filtrate was concentrated under reduced pressure to obtain the title compound (8.03 g, 42.9mmol, 87%) as an oily matter. NMR(CDCl3)δ:1.45(9H,s),1.93(1H,brs),2.13-2.22(1H,m),3.67-3.81(3H,m),3.87(1H,q,J=8.8Hz),4.21(1H,br s),4.44(1H,br s). MS(ESI)m/z:188(M++1).
With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0℃; for 19.5h;Reflux; Inert atmosphere; To 699 mg (18.48 mmol) sodium borohydride in 20 mL dry THF under nitrogen, was added 1.15 g (5.74 mmol) (S)-azetidine-1 ,2-dicarboxylic acid 1 -te/f-butyl ester and the reaction was cooled to 0 C, 1.72 g (6.78 mmol) iodine in 10 mL dry THF was added dropwise over 30 minutes, the reaction mixture was allowed to warm to room temperature, and was heated under reflux for 19 hours. The mixture was cooled to room temperature and 25 mL MeOH was added dropwise over 15 minutes. After evaporation of the solvent, 30 mL KOH (1 M) was added and the mixture was stirred at room temperature for 2 hours. The aqueous phase was extracted with DCM (2 x 75 mL) and the combined organic layers were washed with saturated brine (3 x 50 mL), then dried over MgSO4. After filtration, the solvent was evaporated to give the desired product, which was used for the next step without further purification.
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  • [ 74115-13-2 ]
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  • [ 186593-31-7 ]
YieldReaction ConditionsOperation in experiment
85% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 48h; To a stirred solution of 1-tert-butoxycarbonyl-2 (5)-AZETIDINE (800 mg, 4.3 mmol) and 3-bromo-5- hydroxypyridine (800 mg, 4.6 mmol), and PPh3 (1.69 g, 6.45 mmol) in THF (50 mL) was slowly added DEAD (1.02 mL, 6.45 mmol). The reaction mixture was stirred at room temperature for 48 h, and concentrated in vacuo. The residue was purified by chromatography with hexane-EtOAc (4: 1) to give a light yellow oil (1.25 g, 85%). H NMR (CDC13) 6 8.29 (d, 1H, J= 2.1 Hz), 8. 28 (d, 1H, J= 2.7 Hz), 7.43 (t, 1H, J= 2.4 Hz), 4.51 (M, 1H), 4.34 (M, 1H), 4. 13 (dd, 1H, J= 10.2, 3.0 Hz), 3. 89 (t, 2H, J= 7.5 Hz), 2.42-2. 22 (M, 2H), 1.43 (s, 9H) ; 13C NMR (CDC13) 8 156.05, 155.35, 143.07, 136.58, 123.96, 120.25, 79.75, 68. 90,59. 84, 47.02, 28. 31,18. 88.
70% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; A gram-scale synthesis of sazetidine A is outlined in Figure Ia. The Boc-protected azidityl methyl alcohol 2 and 3 -bromo-5 -hydroxy pyridine (3) are both commercially available. Treatment with PPh3 and DEAD according to the Mitsunobu protocol formed ether derivative 4 in 70% yield. Palladium-mediated coupling of the bromo-substituted pyridine 4 with 5-hexyn-l-ol under modified Sonogashira conditions furnished Boc- protected sazetidine A in 73% yield. Deprotection of the Boc-group with HCl was expected to give sazetidine A in salt form as published in the literature. However, after several <n="43"/>AtIy Docket No.: GUX-023.25 attempts, it was found that the HCl salt, especially on larger scale, was a white solid that could be obtained in only moderate yield by a tedious filtration under an inert atmosphere. Exposure of the material to air immediately resulted in decomposition of the material to a yellow-brown wet solid. Therefore, in order to obtain gram quantities of pure sazetidine A, it was found that it was necessary to treat the deprotected material immediately with NH4OH and then isolated the free base of sazetidine A. This product was then taken up in an aqueous solution of HCl to give a solution of the HCl salt of sazetidine A. This modified method gives purer material and was indeed found to be more potent than that reported in the literature.
64% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20℃;Inert atmosphere; Under N2 stream, triphenylphosphine (7.8 g, 29.7 mmol), 40% diethyl azodicarboxylate (40% solution in toluene, 5.2 mL), and 5-bromo-3-hydroxynicotinic acid (5.2 g, 29.7 mmol) at 0 C were added to a solution of 1 (3.6 g, 19.8 mmol) in THF (20 mL). The mixture was stirred at 0 C for 10 min and then warmed to room temperature and stirred overnight. After the reaction, the solvent was removed under reduced pressure followed by silica gel chromatography (petroleum ether/ethylacetate=1/1) to yield 8 (4.35 g, 12.7 mmol, 64%) as a colorless oil. 1HNMR (500 MHz, CDCl3) δ; 8.29 (t, J=2.6 Hz, 2H), 7.45-7.42 (m, 1H),4.55-4.48 (m, 1H), 4.33 (broad s, 1H), 4.13 (dd, J=7.5, 2.9 Hz, 1H),3.89 (m, 2H), 2.39-2.24 (m, 2H), 1.43 (s, 9H). 13C NMR (125 MHz,CDCl3) δ; 156.1, 155.4, 143.2, 136.7, 124.1, 120.3, 79.9, 69.0, 64.2,59.5, 28.4, 19.0. MS (EI+) m/z; 344 ([M+2]+, 1.97), 342 (M+, 1.92),271 (5.59), 269 (5.81), 243 (5.83), 241 (6.09), 156 (28), 113 (22), 100(34), 57 (1 0 0). HRMS (EI+) m/z; 342.0585 (Calcd: 342.0578 forC14H19N2O3Br). [α]D20=-59.63 (c=2.24, CHCl3).
55% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 10 - 20℃; for 48h;Inert atmosphere; General procedure for Mitsunobu Reaction (Method A). To a mixture of 5-Bromo-3- pyridinol (1.2 equiv) and Ph3P (1.6 equiv) in anhydrous THF taken in a flame-dried flask under N2, N-Boc protected alcohol (1 equiv) was added and the mixture was cooled to - 10 C. Diethyl azodicarboxylate (40% w/v) in toluene (1.6 equiv) was added dropwise to the mixture and was warmed gradually to the room temperature. After 48 h, the reaction mixture was quenched with 1 mL of water and the solvent was removed under reduced pressure. The resulting yellow oil was purified by column chromatography on silica gel to yield 55-60% as a white solid. Example 3(S)-tei"i-butyl-2-((5-bromopyridin-3-yloxy)methyl)azetidine-l-carboxylate (VMY-2-3): Method A was used. Yield 55% (white solid). 1H NMR (400 MHz, CDC13) ? 8.25 - 8.19 (m, 2H), 7.36 (s, 1H), 4.44 (d, J= 5.3, 1H), 4.32 - 4.20 (m, 1H), 4.06 (dd, J = 2.8, 10.1, 1H), 3.81 (t, J= 7.5, 2H), 2.36 - 2.14 (m, 2H), 1.36 (s, 9H). 13C NMR (100 MHz, CDC13 ) ? 156.07,155.41, 143.13, 136.65, 124.02, 120.28, 79.76, 69.00, 59.92,47.14, 28.37, 18.95.HRMS (ESI): exact mass calcd for Ci4Hi9BrN203 [M+H]+, 343.0657, found 343.0670.
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 12a. 5-((2S)-Azetidinylmethyloxy)-3-bromopyridine dibenzoate Triphenylphosphine (4.01 g, 15.3 mmol) and DEAD (2.43 mL, 15.3 mnol) were dissolved in 30 mL of THF at 0 C., and the mixture was stirred for 10 minutes. Samples of 1-t-butyloxycarbonyl-2-(S)-azetidinemethanol (2.86 g, 15.3 mmol, Step 7c above) and 3-bromo-5-hydroxypyridine.(1.51 g, 10.2 mmol, Step 10c above) were added, and the mixture was stirred for 40 hours at room temperature. The volatile components were removed under vacuum, and the residue was triturated with hexane. The separated hexane fraction was concentrated, and the residue was chromatographed (silica gel; hexane/ether, 10:1 to 10:2) to afford 5-bromo-3-((1-t-butyloxycarbonyl-(2S)-azetidinyl)methoxy)pyridine as a colorless oil (1.669 g): 1 H NMR (CDCl3, 300 MHz) δ 1.42 (s, 9H), 2.31 (m, 2H), 3.89 (m, 2H), 4.12 (m, 1 H), 4.322 (m, 1 H), 4.52 (m, 1 H), 7.43 (m, 1 H), 8.29 (m, 2H); MS (CI/NH3) m/z 344 (M+H)+.

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  • (S)-2-(2-Bromo-pyridin-3-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester [ No CAS ]
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  • [ 74115-12-1 ]
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YieldReaction ConditionsOperation in experiment
88% 39a. 5-chloro-3-(N-t-butoxycarbonyl-2-(S)-azetidinylmethoxy)pyridine An ice-cooled solution of the compound from Example 7b (0.242 g, 1.20 mmol) was allowed to react with 3-chloro-5-hydroxypyridine (0.187 g, 1.40 mmol) under the conditions of Example 2a, except that DEAD was replaced with di-t-butylazodicarbonate, to yield the title compound (0.137 g, 88%) after purification on silica gel (ethyl acetate/hexane 2:1). MS (DCI/NH3) m/e: 299 (M+H)+. 1 H NMR (CDCl3, 300 MHz) δ: 8.25 (d, J=1.38 Hz, 1H), 8.21 (br. s, 1H), 7.29 (t, J=2.2 Hz, 1H), 4.53-4.51 (m, 1H), 4.34-4.33 (m, 1H), 4.13 (dd, J=10.3, 2.9 Hz, 1H), 3.91-3.86 (m, 2H), 2.51 (s, 3H), 2.38-2.29 (m, 2H), 1.43 (s, 9H).
39a. 5-chloro-3-(N-t-butoxycarbonyl-2-(S)-azetidinylmethoxy)pyridine An ice-cooled solution of the compound from Example 7b (0.242 g, 1.20 mmol) was allowed to react with 3-chloro-5-hydroxypyridine (0.187 g, 1.40 mmol) under the conditions of Example 2a, except that DEAD was replaced with di-t-butylazodicarbonate, to yield the title compound (0.137 g, 88%o) after purification on silica gel (ethyl acetate/hexane 2:1). MS (DCI/NH3) m/e: 299 (M+H)+. 1 H NMR (CDCl3,300 MHz) δ: 8.25 (d, J=1.38 Hz, 1H), 8.21 (br. s, 1H), 7.29 (t, J=2.2 Hz, 1H), 4.53-4.51 (m, 1H), 4.34-4.33 (m, 1H), 4.13 (dd, J=10.3, 2.9 Hz, 1H), 3.91-3.86 (m, 2H), 2.51 (s, 3H), 2.38-2.29 (m, 2H), 1.43 (s, 9H).
  • 10
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  • (S)-2-(2-Chloro-pyridin-3-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester [ No CAS ]
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YieldReaction ConditionsOperation in experiment
86% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 48h;Inert atmosphere; General Procedure for the Mitsunobu Reaction. To a mixture of the N-Boc protected alcohol (1.0 equiv), the 5-halogen-3-pyridinol (1.0 equiv), and Ph3P (1.3 equiv) in anhydrous THF (0.1 M) was added DEAD (1.3 equiv) dropwise at 0 C under nitrogen atmosphere. After stirring for 2 days at room temperature, the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel using a gradient of hexane-ethyl acetate (10: 1 to 5: 1) as the eluent to give the product in 68%-90% yield. (S)-tert-butyl-2-((5-iodopyridin-3-yloxy)methyl)azetidine-l-carboxylate ((S)-5). Yield: 86' (white solid). 1H NMR (CDC13, 400 MHz): δ 8.43 (d, 1H, J= 1.2 Hz), 8.30 (d, 1H, J= 2.4 Hz), 7.61 (dd, 1H, J = 2.4, 1.6 Hz), 4.50 (m, 1H), 4.32 (m, 1H), 4.12 (dd, J = 10, 2.8 Hz), 3.88 (m, 2H), 2.31 (m, 2H), 1.43 (s, 9H).
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