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CAS No. : | 71830-08-5 | MDL No. : | MFCD00211289 |
Formula : | C6H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MLLSSTJTARJLHK-UHNVWZDZSA-N |
M.W : | 129.16 | Pubchem ID : | 1502035 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.83 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 33.32 |
TPSA : | 63.32 Ų |
GI absorption : | High |
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) : | -8.9 cm/s |
Log Po/w (iLOGP) : | 0.97 |
Log Po/w (XLOGP3) : | -2.55 |
Log Po/w (WLOGP) : | 0.2 |
Log Po/w (MLOGP) : | 0.0 |
Log Po/w (SILICOS-IT) : | -0.08 |
Consensus Log Po/w : | -0.29 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 1.03 |
Solubility : | 1390.0 mg/ml ; 10.8 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 1.77 |
Solubility : | 7520.0 mg/ml ; 58.2 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.22 |
Solubility : | 213.0 mg/ml ; 1.65 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.07 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-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 |
---|---|---|
100% | With thionyl chloride; at 0 - 65℃; for 20h; | Preparation No.69: Preparation of (l/~,3£)-methyl 3- (dibenzylamino)cyclopentanecarboxylate; Step 1; (IR, 3£)-Methyl 3-aminocyclopentanecarboxylate hydrochloride; A solution of (1 ~,35)-3-aminocyclopentanecarboxylic acid (0.115 g, 0.890 mmol) (PepTech) in MeOH (1.5 mL) was cooled to about 0 C in an ice bath. Thionyl chloride (0.130 mL, 1.781 mmol) was added dropwise. The reaction mixture was stirred at about 0 C for about 2 h, then the reaction mixture was heated at about 65 C for about 18 h until TLC in (3:1 :1 n- BuOH/AcOH/water) showed (Ninhydrin/EtOH visualization) less polar spot forming (Product's Rf=0.428, SM's Rf=0.345). The reaction mixture was cooled down and concentrated to afford ( IR, 3S)-Methyl 3-aminocyclopentanecarboxylate hydrochloride (0.16 g, 0.89 mmol, 100 % yield) as a pale green solid. |
90% | With thionyl chloride; at 70℃; | Into a 100-mL round-bottom flask, was placed a solution of (1R,3S)-3- aminocyclopentane-1-carboxylic acid (500 mg, 3.87 mmol, 1.00 equiv) in methanol (10 mL). This was followed by the addition of sulfuryl dichloride (921 mg, 7.74 mmol, 2.00 equiv) dropwise with stirring at 0 oC. The resulting solution was stirred overnight at 70 oC then concentrated under vacuum. This resulted in 500 mg (90%) of methyl (1R,3S)-3- aminocyclopentane-1-carboxylate hydrochloride as colorless oil |
With thionyl chloride; at 0 - 20℃; | Synthesis 5; (1R,3S)-Methyl S-aminocyclopentanecarboxylate hydrochloride A suspension of <strong>[71830-08-5](1R,3S)-3-aminocyclopentanecarboxylic acid</strong> (500 mg, 3.8 mmol) in methanol (10 ml.) was stirred at O0C and thionyl chloride (1.40 ml_, 19.3 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The resulting clear solution was evaporated, azeotroped with methanol (2 x 5 ml_), air-dried and the title compound obtained as a white powder (680 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44.3% | With potassium carbonate; In N,N-dimethyl-formamide; at 160℃; for 0.5h;Microwave irradiation; | Exemplification of General Procedure L:; Preparation of (lR,3S)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5- yl)phenylamino)cyclopentanecarboxylic acid; 3-(3-Chloro-4-isopropoxyphenyl)-5-(4-fluorophenyl)-l,2,4-oxadiazole (360 mg, 1.082 mmol), (lR,3S)-3-aminocyclopentanecarboxylic acid (154 mg, 1.190 mmol), potassium carbonate (329 mg, 2.380 mmol) and DMF (2 ml) was heated with cooling at 160 0C on the Biotage microwave for 30 minutes. The mixture was diluted with DMSO (6 ml) and MeCN (8 ml), filtered and divided into 8 aliquots for purification by molecular ion directed LCMS. The fractions were combined and evaporated to afford a pale brown solid that was dried in vacuo at about 600C for about 3 hours. This gave (lR,3S)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)- l^^-oxadiazol-S-yOphenylaminoXyclopentanecarboxylic acid (212 mg, 0.480 mmol, 44.3 % yield) as a pale brown solid. LCMS (Table 1, Method a) Rt = 3.49 min, m/z 440.20 (M-H)-. IH NMR (400 MHz, DMSOdelta ppm 4.81 (s, IH), 3.96-3.76 (m, IH), 2.78 (s, IH), 2.42-2.25 (m, IH), 2.12-1.95 (m, IH), 1.89 (d, J = 7.72 Hz, 2H), 1.73-1.61 (m, IH), 1.61-1.48 (m, IH), 1.39-1.30 (m, 7H), 12.22-12.07 (m, IH), 6.73 (d, J = 8.82 Hz, 2H), 6.87-6.79 (m, IH), 7.36 (d, J = 8.63 Hz, IH), 7.87 (d, J = 8.59 Hz, 2H), 7.98 (ddd, J = 9.78, 1.97, 1.06 Hz, 2H). |
44.3% | With potassium carbonate; In N,N-dimethyl-formamide; at 160℃; for 0.5h;microwave irradiation; | Examplification of General Procedure L:; Preparation of (l/~,35)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5- yl)phenylamino)cyclopentanecarb oxylic acid; 3-(3-Chloro-4-isopropoxyphenyl)-5-(4-fluorophenyl)-l,2,4-oxadiazole (360 mg, 1.082 mmol), (1 ~,35)-3-aminocyclopentanecarboxylic acid (154 mg, 1.190 mmol), potassium carbonate (329 mg, 2.380 mmol) and DMF (2 mL) was heated with cooling at about 160 C on the Biotage microwave for about 30 min. The mixture was diluted with DMSO (6 mL) and ACN (8 mL), filtered and divided into 8 aliquots for purification by molecular ion directed LC/MS. The fractions were combined and evaporated to afford a pale brown solid that was dried in vacuo at about 60 C for about 3 h. This gave (lR,3S)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4- oxadiazol-5-yl)phenylamino)cyclopentanecarboxylic acid (212 mg, 0.480 mmol, 44.3 % yield) as a pale brown solid. LC/MS (Table 1, Method a) Rt = 3.49 min, mix 440.20 (M-H)-. 1H NMR (400 MHz, DMSQ ppm 4.81 (s, 1H), 3.96-3.76 (m, 1H), 2.78 (s, 1H), 2.42-2.25 (m, 1H), 2.12- 1.95 (m, 1H), 1.89 (d, J = 7.72 Hz, 2H), 1.73-1.61 (m, 1H), 1.61-1.48 (m, 1H), 1.39-1.30 (m, 7H), 12.22-12.07 (m, 1H), 6.73 (d, J = 8.82 Hz, 2H), 6.87-6.79 (m, 1H), 7.36 (d, J = 8.63 Hz, 1H), 7.87 (d, J = 8.59 Hz, 2H), 7.98 (ddd, J = 9.78, 1.97, 1.06 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; at 0 - 20℃; | To a solution of (lS,3R)-3-aminocyclopentanecarboxylic acid (1.0 g, 7.4 mmol) in dry MeOH (10 mL) under N2 at 0 C was added thionyl chloride (2.7 mL, 36.8 mmol) dropwise. The reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction was concentrated in vacuo. The resultant residue was washed with anhydrous diethyl ether (3x30 mL) and dried under high vacuum to afford 1.87 g of (lS,3R)-3-amino-cyclopentanecarboxylic acid methyl ester as the HCl salt that was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34.2% | Example No.16: Synthesis of (l/?,3S)-3-(5-pentylpyrimidin-2-ylamino)cyclopentanecarboxylic acid; 2-Chloro-5-n-pentylpyrimidine (100 mg, 0.542 mmol), (li?,3S>;3- aminocyclopentanecarboxylic acid (84 mg, 0.650 mmol), potassium carbonate (165 mg, 1.191 mmol) and DMSO (2170 muL)/water (180 mul) were heated in a Biotage microwave at about 170 C for about 20 min. The reaction mixture was reheated at 170 C for about 10 min with no significant change in LC/MS. The mixture was cooled down and the reaction mixture was partitioned between DCM (25 mL) and HCl (IM, 25 mL), the aqueous layer was extracted by DCM (25 mL), the combined organic layers were washed with brine (25 mL), filtered through a Biotage Phase separator and concentrated. The crude product was added to a silica gel column and eluted with MeOH/DCM (0-10%, 30 min). Collected fractions containing the correct MW by LC/MS were combined, concentrated and dried in a vacuum oven at about 30 C to provide (lR,3S)-3-(5-pentylpyrimidin-2-ylamino)cyclopentanecarboxylic acid (54 mg, 0.185 mmol, 34.2% yield) as a viscous oil. 1H NMR (400 MHz, DMSO-d6): delta 12.06 (bs, IH), 8.11 (s, 2H), 6.90 (d, J = 7.2 Hz, IH), 4.23 - 4.05 (m, IH), 2.81 - 2.64 (m, IH), 2.35 (t, J = 7.6 Hz, 2H), 2.19 (dt, J = 12.5, 7.3 Hz, IH), 1.98 - 1.74 (m, 3H), 1.64 (dt, J = 12.6, 9.1 Hz, IH), 1.58 - 1.43 (m, 3H), 1.36 - 1.18 (m, 4H), 0.86 (t, J = 7.0 Hz, 3H). LC/MS (Table 2, Method f) R4 = 1.26 min; MS Wz 278.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | Step 2: Preparation of 3-(S)-[2-r7,8-Dimethyl-2,4-dioxo-3,4-dihvdro-2H- benzo[glpteridin-10-yl)-ethylaminol-(R)-cvclopentanecarboxyIic acid trifluoro-acetic acid salt; [0106] To a suspension of 2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)acetaldehyde (100 mg, 0.35 mmol) in methanol (10 mL) is added 3-amino- cyclopentanecarboxylic acid (100 mg, 0.77 mmol) at room temperature. Glacial acetic acid (7 drops) is added and allowed to stir at room temperature for 3 h. Sodiumcyanoborohydride (48 mg, 0.77 mmol) is added and the solution is stirred for 16 h. The reaction mixture is concentrated, and the residue is dissolved in DMSO (5 mL), filtered, and purified by preparative HPLC (Method 1). 3-(S)-[2-(7,8-Dimethyl-2,4-dioxo-3,4- dihydro-2H-benzo[g]pteridin-10-yl)-ethylamino]-(R)-cyclopentanecarboxylic acid (8.2 mg) is isolated following lyophilization of the appropriate fractions (Yield: 6.0%). 1H NMR (300 MHz, DMSO-d6) delta 1.7 (m, 2H), 1.85 (m, 1H), 2.03 (m, 2H), 2.10 (m, 1H), 2.43 (s, 3H), 2.53 (s, 3H), 2.90 (m, 2H), 3.73 (m, 2H)5 4.92 (m, 2H), 7.78 (s, 1H), 7.98 (s, 1H), 8.66 (m, 2H), 11.49 (s, 1H), 12.35 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With sodium hydroxide; In tetrahydrofuran; water; at 20℃; | Example IVExample IV.1(1 R,3S)-3-Propionylamino-cvclopentanecarboxylic acid 100.0 mg (0.77 mmol) (1 R,3S)-3-Aminocyclopentane carboxylic acid is stirred in 2.0 mL THF and 0.77 mL (1 .55 mmol) sodium hydroxide solution (2 mol/l). 74.0 mu (0.85 mmol) Propionyl chloride is added drop wise and the mixture is stirred at RT over night. The solvent is evaporated. The mixture is stirred at RT over night. The product is purified by RP-HPLC (water + 5-95% acetonitrile (with addition of 0.1 % TFA)) and lyophilized.Yield: 80.0 mg (56% of theory) Ell Mass spectrum: m/z = 184 [M-H]~ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With thionyl chloride; for 3h;Reflux; | Example 34(1R,3S)-3-Acetamido-N-(4-(4-fluoro-2-methoxyphenyl)pyridin-2-yl)cyclo-pentanecarboxamideStep A: Preparation of (1R,3S)-Methyl 3-aminocyclopentanecarboxylate. Thionyl chloride (1.30 ml, 18.2 mmol) was added to a stirred solution of <strong>[71830-08-5](1R,3S)-3-amino cyclo pentyl carboxylic acid</strong> (2.00 g, 12.1 mmol) in MeOH (20 ml) and refluxed for 3 h. The reaction mixture was concentrated under reduced pressure and co-distilled with toluene to afford 1.9 g (87%) of (1R,3S)-methyl 3-aminocyclopentanecarboxylate as off-white solid. |
To a solution of <strong>[71830-08-5](1R,3S)-3-aminocyclopentanecarboxylic acid</strong> (27.1 mmol, 3.5 g) in MeOH (35 mL) at 0 C was added SOd2 (54.2 mmol, 6.4 g). The mixture was stirred at 75C for 16 h. The mixture was concentrated. The residue was suspended in DCM (30 mL) and ACN (30 mL) and treated with Na2CO3 (7.9 g, 75 mmol) and trimethylamine ( 3 mL). The mixture was stirred at room temperature for 16h. The mixture was filtered and concentrated. The product was used in the next step without further purification. ESI: m/z 144.3 (m+1)t |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | A mixture of amino acid 16 (1.0 equiv), fluorobenzonitrile 15 (1.0 equiv), and potassium carbonate (milled 300 mesh, 2.2 equiv) in DMSO-water (20:1; 6 mL/g of 15) was heated to about 105 C. with vigorous agitation until the reaction was complete (in process test by HPLC, typically about 16-20 h). The reaction mixture was cooled, diluted with MTBE (5 mL/g of 16) and water (10 mL/g of 16). The mixture was cooled to about 10 C. and concentrated HCl (0.7 g/g of 16) was added to dissolve solids. The aqueous layer was separated and the organic was extracted with 5% potassium carbonate solution. The product was precipitated via addition of concentrated HCl to the combined aqueous layer to achieve pH 4-6. The product slurry was then cooled to about 10 C. The product was filtered, washed with water (5 mL/g 12) and dried at 55 C. under vacuum. The yield for the amination step is typically 80%.1H NMR (DMSO-d6, delta, ppm) 1.50 (1H), 1.60 (1H), 1.84 (2H), 1.96 (1H), 2.30 (1H), 2.74 (1H), 3.77 (1H), 6.60 (2H), 6.72 (1H), 7.41 (2H), 12.08 (1H). HPLC Method 4 Rt 12.0 min. | |
55.9% | With potassium carbonate; In water; dimethyl sulfoxide; at 100℃; for 16h; | Preparation No.40: (1R, 3»S)-3-(4-cyanophenylamino) cyclopentane carboxylic acid; To a round bottom flask was added 4-fluorobenzonitrile (1.705g, 14.08 mmol), (IR, 3S)-3- aminocyclopentanecarboxylic acid (2 g, 15.49 mmol), potassium carbonate (4.28 g, 31 mmol), DMSO (45 mL) and water (1 mL). The mixture was heated at about 100 C for about 16 h. The mixture was then cooled to ambient temperature and partitioned between water (250 mL) and EtOAc (250 mL). The aqueous layer was extracted with EtOAc (2 x 100 mL). The combined organic layers were dried over Na2S04, filtered and concentrated to dryness to yield (IR, 3S)-3-(4-cyanophenylamino) cyclopentane carboxylic acid (1.83g, 7.87mmol, 55.9%) as an off-white solid. LC/MS (Table 1, Method b) Rt = 1.94 min, mix 231 (M+H) +. .H NMR (400 MHz, DMSO-rff) delta ppm 12.1 (s, 1H), 7.44-7.42 (d, 2H), 6.74-6.72 (d, 1H), 6.63-6.61 (d, 2H), 3.81-3.74 (m, 1H), 2.79-2.71 (m, 1H), 2.37-2.27 (m, 1H), 2.01-1.93 (m, 1H), 1.89-1.83 (m, 2H), 1.65-1.58 (m, 1H), 1.54-1.45 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38.5% | Example No.50: (l ~,3»S)-3-(4-(3-(4-(4,4-Difluoropiperidin-l-yl)-3-(trifluoromethyl)phenyl)- l,2,4-oxadiazol-5-yl)phenylamino)cyclopentanecarboxylic acid acetate salt; 3-(4-(4,4-Difluoropiperidin-l-yl)-3-(trifluoromethyl)phenyl)-5-(4-fluorophenyl)-l,2,4- oxadiazole (503 mg, 1.177 mmol), (1 ~,35)-3-aminocyclopentanecarboxylic acid (167 mg, 1.295 mmol), potassium carbonate (358 mg, 2.59 mmol) and DMF (2 mL) was heated with cooling at about 160 C on the Biotage microwave for about 30 min. The mixture was diluted with DMSO (6 mL) and MeCN (8 mL), filtered and divided into 8 aliquots for purification by molecular ion directed LC/MS. The fractions were combined and evaporated to afford a pale brown solid that was dried in vacuo at about 60 C for about 3 h to afford (lR,3S)-3-(4-(3-(4- (4,4-difluoropiperidin-l-yl)-3-(trifluoromethyl)phenyl)-l,2,4-oxadiazol-5- yl)phenylamino)cyclopentanecarboxylic acid (243 mg, 0.453 mmol, 38.5 % yield) as an off- white solid as the acetate salt. LC/MS (Table 1, Method g) R, = 3.06 min.; MS m/z: 535.2 (M-H)1H NMR (400 MHz, DMSO) delta ppm 7.73 (d, J = 8.23 Hz, 1H), 7.86 (d, J = 8.85 Hz, 2H), 8.29-8.21 (m, 2H), 2.81-2.68 (m, 1H), 2.30 (d, J = 12.64 Hz, 1H), 2.10 (ddd, J = 13.96, 10.71, 5.50 Hz, 4H), 1.98 (s, 1H), 1.92-1.81 (m, 2H), 1.66 (d, J = 12.66 Hz, 1H), 1.52 (s, 1H), 3.09- 3.04 (m, 4H), 3.87-3.79 (m, 1H), 2.52 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Synthesis of DD2: (lR,3S)-3-(4-Cyano-2-methyl-phenylamino)-c; A solution of DDI (lR,3S)-3-Amino-cyclopentanecarboxylic acid (5.89 g, 45.6 mmol) and 4- fluoro-3-methylbenzonitrile (5.60g, 41.4 mmol) in DMSO (140 mL) and water (11.67 mL) was treated with potassium carbonate (12.60 g, 91 mmol) and the mixture was heated to about 110 °C under nitrogen overnight . The solution was cooled to room temperature and diluted with water, washed with ether then acidified to pH=2 with concentrated HC1. The product was extracted with ethyl acetate, the combined ethyl acetate layers were washed with saturated NaCl solution, dried over sodium sulfate, filtered and concentrated to about 100 mL. Hexane (100 mL) was added and the solution concentrated until product comes out of solution. Filtered off solids and concentrated the filtrate to a gum which was dissolved in methanol 40mL, and water and concentrated until crystals formed. A second crop of solids was filtered off combined with the first crop then dried in a vacuum overnight to give 5.78 g of (lR,3S)-3-(4-Cyano-2-methyl-phenylamino)-cyclopentanecarboxylic acid ( DD2, 57percent yield ) LC/MS(ESI): m/z 245.2 (M+H), Rt: 0.78 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.33% | With potassium carbonate; In N,N-dimethyl-formamide; at 160℃; for 0.5h;microwave irradiation; | Example No.48: (1^35)-3-(4-(3-(4-((5)-Tetrahydrofuran-3-yloxy)-3-(trifluoromethyl)phenyl)-l,2,4-oxadiazol-5-yl)phenylamino)cyclopentanecarboxylic acid; (S)-5 -(4-fluorophenyl)-3 -(4-(tetrahydrofuran-3 -yloxy)-3 -(trifluoromethyl)phenyl)- 1 ,2,4- oxadiazole (350 mg, 0.888 mmol), (1 ~,3.S)-3-aminocyclopentanecarboxylic acid (115 mg, 0.888 mmol), potassium carbonate (270 mg, 1.953 mmol) and DMF (2 mL) was heated with cooling at about 160 C on the Biotage microwave for about 30 min. The mixture was diluted with DMSO (6 mL) and MeCN (8 mL), filtered and divided into 8 aliquots for purification by molecular ion directed LC/MS. The fractions were combined and evaporated to afford a pale brown solid that was dried in vacuo at about 60 C for about 3 h to afford (lR,3S)-3-(4-(3-(4- ((S)-tetrahydrofuran-3-yloxy)-3-(trifluoromethyl)phenyl)-l,2,4-oxadiazol-5- yl)phenylamino)cyclopentanecarboxylic acid (43 mg, 0.083 mmol, 9.33 % yield) as a pale brown solid. NMR showed the presence of ammonium acetate and so the compound was dried in vacuo at about 100 C for about 3 h to afford (lR,3S)-3-(4-(3-(4-((S)-tetrahydrofuran-3- yloxy)-3-(trifluoromethyl)phenyl)-l,2,4-oxadiazol-5-yl)phenylamino)cyclopentanecarboxylic acid (43 mg, 0.083 mmol, 9.33 % yield) as an off-white solid. LC/MS (Table 1, Method g) Rt = 2.61 min.; MS m/z: 504.2 (M+H)+. 1H NMR (400 MHz, DMSO) d ppm 7.48 (d, J = 8.85 Hz, 1H), 7.03-6.89 (m, 1H), 6.72 (d, J = 8.94 Hz, 2H), 7.87 (d, J = 8.88 Hz, 2H), 8.20 (d, J = 2.03 Hz, 1H), 8.27 (dd, J = 8.73, 2.06 Hz, 1H), 5.37-5.27 (m, 1H), 3.98 (dd, J = 10.41, 4.47 Hz, 1H), 3.90-3.74 (m, 4H), 2.75 (t, J = 8.31 Hz, 1H), 2.30 (td, J = 11.68, 6.98 Hz, 2H), 2.10- 1.92 (m, 2H), 1.92-1.81 (m, 2H), 1.68 (dd, J = 7.98, 4.74 Hz, 1H), 1.55 (dd, J = 12.18, 6.65 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22.93% | With potassium carbonate; In N,N-dimethyl-formamide; at 160℃; for 0.5h;microwave irradiation; | Example No.49: (l ~,3»S)-3-(4-(3-(4-(4-Fluoropiperidin-l-yl)-3-(trifluoromethyl)phenyl)- l,2,4-oxadiazol-5-yl)phenylamino)cyclopentanecarboxylic acid; 5-(4-Fluorophenyl)-3-(4-(4-fluoropiperidin- 1 -yl)-3-(trifluoromethyl)phenyl)- 1 ,2,4-oxadiazole (420 mg, 1.026 mmol), (1 ~,35)-3-aminocyclopentanecarboxylic acid (146 mg, 1.129 mmol), potassium carbonate (312 mg, 2.257 mmol) and DMF (2 mL) was heated with cooling at about 160 C on the Biotage microwave for about 30 min. The mixture was diluted with DMSO (6 mL) and MeCN (8 mL), filtered and divided into 8 aliquots for purification by molecular ion directed LC/MS. The fractions were combined and evaporated to afford a pale brown solid that was dried in vacuo at about 60 C for about 3 h to afford (lR,3S)-3-(4-(3-(4- (4-fluoropiperidin-l-yl)-3-(trifluoromethyl)phenyl)-l,2,4-oxadiazol-5- yl)phenylamino)cyclopentanecarboxylic acid (122 mg, 0.235 mmol, 22.93 % yield) as an off- white solid. LC/MS (Table 1, Method f) R, = 3.05 min.; MS m/z: 517.17 (M-H) 1H NMR (400 MHz, DMSO) delta ppm 6.83 (d, J = 6.67 Hz, 1H), 6.72 (d, J = 8.92 Hz, 2H), 8.28-8.21 (m, 2H), 7.87 (d, J = 8.86 Hz, 2H), 7.67 (d, J = 8.40 Hz, 1H), 12.16-12.05 (m, 1H), 4.97-4.75 (m, 1H), 3.84 (d, J = 6.98 Hz, 1H), 3.08 (t, J = 9.04 Hz, 2H), 1.65 (d, J = 12.27 Hz, 1H), 1.52 (s, 1H), 2.31 (s, 1H), 2.11-1.92 (m, 3H), 1.92-1.79 (m, 4H), 2.97-2.85 (m, 2H), 2.83-2.69 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With water; potassium carbonate; In dimethyl sulfoxide; at 170℃; for 1h;microwave irradiation; | Preparation No.60b: Preparation of (l^,3S)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4- oxadiazol-5-yl)-2-ethynylphenylamino)cyclopentanecarboxylic acid; A 20 mL microwave reaction vial equipped with pressure-releasing septa cap was charged with 3-(3-chloro-4-isopropoxyphenyl)-5-(4-fluoro-3-((trimethylsilyl)ethynyl)phenyl)-l,2,4- oxadiazole (0.295 g, 0.688 mmol), (1 ~,35)-3-aminocyclopentanecarboxylic acid (0.098 g, 0.756 mmol), and potassium carbonate (0.209 g, 1.513 mmol) in water (0.344 mL) and DMSO (3.09 mL) to give a tan suspension. The reaction mixture was heated at about 170 C for about 1 h using simultaneous heating while cooling. The reaction mixture was diluted with 10 mL of water and diluted with EtOAc. The solution was washed with 1M HC1 solution (3 x 50 mL) and saturated NaCl solution (1 x 50 mL). The organic phase was dried over MgSO t, filtered and concentrated to give a solid that was triturated with MeOH, filtered, and dried open to the air to give 256 mg of a solid that was suspended in DMSO and filtered, washed with IN HC1 solution and dried open to the air to afford (lR,3S)-3-((4-(3-(3-chloro-4- isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)phenyl)(methyl)amino)cyclopentanecarboxylic acid (220 mg, 64%) as a white solid. LC/MS (Table 1, Method g) Rt = 1.63 min, m/z 466 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.7% | With N-ethyl-N,N-diisopropylamine; In ethanol; at 80℃; for 3h; | To a solution of l-Benzenesulfonyl-4-chloro-5-nitro-lH-pyrrolo[2,3-b]pyridine (3.35 g, 10.23 mmol) in ethanol (50 mL) was added (lR,3S)-3-Amino-cyclopentanecarboxylic acid (1.20 g, 9.30 mmol) and Diisopropylethylamine (3.96 g, 30.96 mmol). The reaction mixture was heated at 80 C for 3 h. After being cooled room temperature, the mixture was condensed and the residue was purified by column chromatography on silica gel (eluting with 10%> to 30%> ethyl acetate in petroleum ether) to give compound 3 (4.00 g, yield 93.7%). LCMS (Method K, ESI): RT = 1.300 min, m+H = 430.9. This material was used in the next step below without additional characterization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; In methanol; for 1h; | [0206] Biphenyl carboxaldehyde (2.82 g, 15.5 mmol) was added to a stirred solution of (IR, 35)-3-aminocyclopentanecarboxylic acid (2.0g, 15.5 mmol) in anhydrous methanol (50 mL) and acetic acid (2 mL). After stirring at room temperature for 1 hour, sodium triacetoxyborohydride (6.57 g, 31 mmol) was added portion wise over 10 minutes and the reaction was stirred at room temperature for 4 hours, diluted with saturated aqueous sodium chloride, and extracted with ethyl acetate (3 x 30 mL). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give crude (li?,35)-3-(biphen-4-ylmethyl-amino)- cyclopentane carboxylic acid, which was used in the next step without further purification; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | In 1-methyl-pyrrolidin-2-one; at 120 - 150℃; for 4h;Microwave irradiation; | Intermediate 47 (100 mg, 0.24 mmol) and (li?,35)-3-aminocyclopentane- carboxylic acid (47 mg, 0.36 mmol) were dissolved in NMP (2 mL) and heated under microwave irradiation at 120C for 1 h, then at 150C for an additional 2 h. Further (li?,35)-3-aminocyclopentanecarboxylic acid (25 mg, 0.19 mmol) was added and the mixture was heated at 150C under microwave irradiation for 1 h. The reaction mixture was partitioned between DCM (4 mL) and water (3 mL), then the organic layer was separated, dried over Na2S04 and concentrated under reduced pressure. The residue was purified by preparative HPLC (Method D), to afford the title compound (18 mg, 15%) as an off-white solid. deltaEta (500 MHz, DMSO-d6) 8.26 (s, 2H), 7.99 (s, 1H), 7.43-7.08 (m, 6H), 6.93 (d, J 7.1 Hz, 1H), 4.28 (s, 2H), 4.21 (q, J7.4 Hz, 1H), 2.74 (p, J 8.7 Hz, 1H), 2.28 (s, 3H), 2.24 (s, 3H), 2.21 (dd, J 13.6, 6.5 Hz, 1H), 1.93 (dd, J 12.5, 5.6 Hz, 1H), 1.85 (td, J 14.7, 13.7, 6.5 Hz, 2H), 1.70 (dt, J 12.6, 9.0 Hz, 1H), 1.62-1.52 (m, 1H). Method A HPLC-MS: MH+ mlz 508, RT 3.26 minutes (100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43%; 44% | With water; benzylamine; lipase B from Candida antarctica; In isopropyl alcohol; at 60℃; for 55h;Enzymatic reaction; | Via the procedure described above,13 the reaction of racemic (±)-2 (100mg, 0.71mmol), benzylamine (79muL, 0.71mmol.) and H2O (6.4muL, 0.35mmol) in i-Pr2O (10mL) in the presence of CAL-B (300mg, 30 mgmL-1) at 60C after 55h afforded the unreacted (1R,4S)-2 [44mg, 44%; viscous oil, [alpha]D25=+49.8 (c 0.72, CHCl3), ee=96%] and amino acid (1R,3S)-8 [39mg, 43%; [alpha]D25=-11.0 (c 0.30, H2O), ee=99%; lit.13=-10.6 (c 0.35, H2O), ee=98%; mp >260C with decomposition (recrystallized from H2O/Me2CO), lit.13 mp >260C with decomposition (recrystallized from H2O/Me2CO)]. The 1H NMR (400MHz, CDCl3, 25C, TMS) data for (1R,4S)-2: delta=1.35-1.96 (m, 6H, 3×CH2); 2.75-2.86 (m, 1H, CHCO); 3.95-4.06 (m, 1H, CHN); 4.49-4.87 (m, 2H, CH2OH). Analysis: calculated for C7H11NO2: C, 59.56; H, 7.85; N, 9.92; found: C, 59.62; H, 7.89; N, 9.86. The 1H NMR (400MHz, D2O) data for (1R,3S)-8: delta=1.72-2.41 (m, 6H, 3×CH2); 2.84-2.96 (m, 1H, CHCOOH); 3.79-3.89 (m, 1H, CHNH2). Analysis: calculated for C6H11NO2: C, 55.80; H, 8.58; N, 10.84; found: C, 55.78; H, 8.60; N, 10.84. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; benzylamine; lipase B from Candida antarctica; In isopropyl alcohol; at 60℃; for 48h;Enzymatic reaction; | General procedure: In a typical small-scale experiment, to the racemic substrate (0.05M solution) in i-Pr2O (1mL) CAL-B (30mg), H2O (0.5equiv) and then benzylamine (1equiv) were added. The mixture was shaken (167rpm) at 60C. The progress of the reaction was followed by taking samples from the reaction mixtures and analyzing them by a GC method on a Chrompack Chirasil-Dex CB column [140C for 25min?190C (temperature rise 20Cmin-1; 140kPa; retention times (min), (1S,4R)-1: 5.84 (antipode: 5.66)], (1R,4S)-2: 7.47 (antipode: 7.11)]. The ee values for the product gamma-amino acids [after pre-column derivatization16 with CH2N2 (Caution derivatization with CH2N2 should be performed under a well-ventillating hood)] were determined by a GC method [120C for 25min?160C (temperature rise 10Cmin-1; 140kPa; retention times (min), (1S,4R)-6: 27.38 (antipode: 27.84)], (1R,3S)-8: 28.74 (antipode: 28.98)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; lipase B from Candida antarctica; In isopropyl alcohol; at 60℃; for 48h;Enzymatic reaction; | General procedure: In a typical small-scale experiment, to the racemic substrate (0.05M solution) in i-Pr2O (1mL) CAL-B (30mg), H2O (0.5equiv) and then benzylamine (1equiv) were added. The mixture was shaken (167rpm) at 60C. The progress of the reaction was followed by taking samples from the reaction mixtures and analyzing them by a GC method on a Chrompack Chirasil-Dex CB column [140C for 25min?190C (temperature rise 20Cmin-1; 140kPa; retention times (min), (1S,4R)-1: 5.84 (antipode: 5.66)], (1R,4S)-2: 7.47 (antipode: 7.11)]. The ee values for the product gamma-amino acids [after pre-column derivatization16 with CH2N2 (Caution derivatization with CH2N2 should be performed under a well-ventillating hood)] were determined by a GC method [120C for 25min?160C (temperature rise 10Cmin-1; 140kPa; retention times (min), (1S,4R)-6: 27.38 (antipode: 27.84)], (1R,3S)-8: 28.74 (antipode: 28.98)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.73% | With triethylamine; In N,N-dimethyl-formamide; at 60℃; for 12h; | To a solution of (2,5-dioxopyrrolidin-1-yl) 4-[[4-(trifluoromethyl)phenyl]methyl]pyrazolo[1,5-a]pyridine-3-carboxylate (50 mg, 119.81 umol, 1 eq) and (1R,3S)-3- aminocyclopentanecarboxylic acid (77.37 mg, 599.04 umol, 5 eq) in DMF (2 mL) was added Et3N (218.22 mg, 2.16 mmol, 300.16 uL, 18 eq). The mixture was stirred at 60C for 12 hr. Several new peaks were shown on LC-MS and 64% of desired compound was detected. The reaction mixture was concentrated under reduced pressure to remove DMF. The residue was diluted with H2O 10 mL and extracted with EA 15 mL (5 mL × 3). The combined organic layers were washed with brine 5 mL, dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (HCl condition). Compound (1R,3S)-3-[[4-[[4- (trifluoromethyl) phenyl]methyl]pyrazolo[1,5-a]pyridine-3- carbonyl]amino]cyclopentanecarboxylic acid (2.5 mg, 5.67 umol, 4.73% yield, 97.8% purity) was obtained as a white solid. LCMS for product (ESI): m/z 432.0 [M+H]+.1H NMR (400 MHz, DMSO-d6) d = 12.12 (br s, 1H), 8.67 (d, J = 6.8 Hz, 1H), 8.20 - 8.15 (m, 2H), 7.56 (d, J = 8.0 Hz, 2H), 7.32 (d, J = 7.2 Hz, 3H), 7.03 (t, J = 7.2 Hz, 1H), 4.65 (s, 2H), 4.21 - 4.13 (m, 1H), 2.78 - 2.69 (m, 1H), 2.17-2.14 (m, 1H), 1.89 - 1.79 (m, 3H), 1.67 - 1.63 (m, 1H), 1.51 - 1.43 (m, 1H). |
Tags: 71830-08-5 synthesis path| 71830-08-5 SDS| 71830-08-5 COA| 71830-08-5 purity| 71830-08-5 application| 71830-08-5 NMR| 71830-08-5 COA| 71830-08-5 structure
[ 1096155-68-8 ]
(1S,3R)-3-Aminocyclopentanecarboxylic acid hydrochloride
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cis-3-Aminocyclopentanecarboxylic acid hydrochloride
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(1S,3S)-3-Aminocyclopentanecarboxylic acid hydrochloride
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