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CAS No. : | 36520-39-5 | MDL No. : | MFCD00191762 |
Formula : | C3H8ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HGQULGDOROIPJN-UHFFFAOYSA-N |
M.W : | 93.56 | Pubchem ID : | 12308726 |
Synonyms : |
Trimethyleneimine hydrochloride;Azetidine hydrochloride
|
Num. heavy atoms : | 5 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 28.1 |
TPSA : | 12.03 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.35 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.73 |
Log Po/w (WLOGP) : | 0.4 |
Log Po/w (MLOGP) : | 0.35 |
Log Po/w (SILICOS-IT) : | 1.37 |
Consensus Log Po/w : | 0.57 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.88 |
Solubility : | 12.3 mg/ml ; 0.132 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.56 |
Solubility : | 25.7 mg/ml ; 0.275 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.58 |
Solubility : | 24.8 mg/ml ; 0.265 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: methyl 7-bromoquinoline-2-carboxylate; azetidine hydrochloride With chloro(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) 2nd generation; caesium carbonate In <i>tert</i>-butyl alcohol at 100℃; for 16h; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride; water at 20℃; | 34.1 Step 1: 7-Azetidin-1-ylquinoline-2-carboxylic acid A mixture of methyl 7-bromoquinoline-2-carboxylate (40.0 mg, 0.15 mmol), dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine-(2'-aminobiphenyl-2-yl)(chloro)palladium (1:1) (23.4 mg, 0.030 mmol) and Cs2CO3 (0.17 g, 0.53 mmol) in a sealed tube was evacuated and backfilled with N2. A solution of azetidine hydrochloride (25.3 mg, 0.27 mmol) in anhydrous t-BuOH (0.62 mL) was added. The resulting reaction mixture was heated to 100° C. and stirred for 16 h. The reaction mixture was cooled to room temperature, neutralized with 4M HCl and diluted with EtOAc. The aqueous layer was extracted with EtOAc (2*) to remove impurities. The solvents and water were removed under reduced pressure. The residue was diluted with THF, dried, filtered and concentrated to give the sub-title compound as a yellow solid (30 mg, 91%). LCMS calc. for C13H13N2O2 (M+H)+: m/z=229.1. Found: 229.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium t-butanolate; XPhos In toluene at 80℃; for 12h; Inert atmosphere; | 18 Synthesis of 147-B Synthesis of 147-B. A mixture of 147-A (600 mg, 2.4 mmol), azetidine hydrochloride (659 mg, 7.08 mmol), t-BuONa (680 mg, 7.08 mmol), Pd2(dba)3 (216 mg, 0.24 mmol) and XPhos (225 mg, 0.47 mmol) in toluene (12 mL) was stirred at 80 oC for 12 h under Ar atmosphere. The mixture was diluted with EtOAc (30 mL) was added and the solution was washed with brine (40 mL × 3). The organic layer was dried over anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 50 : 1 ~ 10 : 1) to give 147-B (500 mg, 77%) as a yellow solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.7% | With triethylamine In tetrahydrofuran; water | A91.5 Step-5. Synthesis of l-(4-bromobenzenesulfonyl)azetidine (A91.10) A solution of 4-bromobenzene-l-sulfonyl chloride (A91.8) (10 g, 39.1 mmol) in tetahydrofuran (200 mL) was added dropwise to a solution of azetidine hydrochloride (A91.9) (7.31 g, 7.31 g) and triethylamine (15.7 g, 156 mmol, 21.6 mL) in water (100 mL) at 0 OC. The solution was stirred for 12 hours at room temperature and evaporated. The resulting mass was suspended in water (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with water (200 mL), 5% aq solution of hydrochloric acid (200 mL), brine (200 mL), dried over sodium sulfate and evaporated under reduced pressure to afford l-(4- bromobenzenesulfonyl)azetidine as white powder (A91.10) (10 g, 36.2 mmol, 95% purity, 88.7% yield). |
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