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CAS No. : | 1174020-30-4 | MDL No. : | MFCD12756143 |
Formula : | C9H17FN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DXQXHFOCKKIWJL-RQJHMYQMSA-N |
M.W : | 204.24 | Pubchem ID : | 45489886 |
Synonyms : |
|
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: |
* 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 |
---|---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate; N,N-dimethyl-formamide at 40℃; for 2h; | To a stirred solution of (3S,4R)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate and 38 or ER-895194 (15 mg, 0.050 mmol) in DMF (0.2 ml) was added propylphosphonic anhydride (0.2 g of a 50% solution in EtOAc) at 40° C. for 2 h. The reaction mixture was passed over a silica gel plug (3 g, eluting with heptane-EtOAc 1:3), and then further purified by preparative TLC (n-heptane/EtOAc 1:4) to give corresponding amide, 78, as yellow/green oil (11.2 mg, 0.023 mmol, 56% yield in 2 steps). The 1H-NMR & HPLC matched with Compound 78 as described earlier thus the absolute stereochemistry of ER-899742 was confirmed indirectly. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1H-imidazole; thionyl chloride; triethylamine / dichloromethane / 1 - 20 °C 2.1: rhodium(III) chloride hydrate; sodium periodate / acetonitrile; water; 1,2-dichloro-ethane / 18 h / 2 - 18 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Reflux 3.2: 2 h 4.1: hydrogen; palladium 10% on activated carbon / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: rhodium(III) chloride hydrate; sodium periodate / acetonitrile; water; 1,2-dichloro-ethane / 18 h / 2 - 18 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Reflux 2.2: 2 h 3.1: hydrogen; palladium 10% on activated carbon / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Reflux 1.2: 2 h 2.1: hydrogen; palladium 10% on activated carbon / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.9% | With palladium 10% on activated carbon; hydrogen In ethanol | (3S,4R)-tert-butyl 3-(benzylamino)-4-fluoropyrrolidine-1-carboxylate, 81 (16 mg, 0.054 mmol) was subjected to hydrogenolysis with 10 wt % Pd-C(10 mg) in ethanol (3 ml). The completed reaction mixture was filtered, concentrated and azeotroped with CDCl3 to provide (3S,4R)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate, 83 (8.3 mg, 0.041 mmol, 75.9% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With palladium on activated charcoal; hydrogen In methanol; water at 20℃; for 16h; | 79 Procedure for the preparation of compound 79a : To a mixture of compound 79a1 (120 mg, 0.59 mmol) in methanol (3 mL) was added palladium on carbon (40 mg) and formaldehyde (0.3 mL, 37%aqueous solution), the resulting mixture was stirred at 20 °C for 16 hours under hydrogen atmosphere. The mixture was filtered, the filtrate was concentrated in vacuum to afford compound 79a2 (120 mg, 88% yield) as a white solid. LCMS: R t = 1.10 min in 3 min chromatography (3min-5-95%MeCN in water (0.02%FA), Waters Acquity UPLC BEH C18 1.7um, 2.1*50 mm, 40°C), MS (ESI) m/z= 233.2 [M+H] +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.5% | With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate In 1,4-dioxane at 85℃; Inert atmosphere; | 75.1 Step 1: preparation of tert- butyl (3S',4 R')-3-(((4i?,10b5 -2-benzyl-4-methyI- l,2,3,4,6,10b-hexahydropyrazino[2,l-a]isoindol-8-yi)amino)-4-fluoropyrrolidine-l- carboxylate (compound 75a) To a solution of fert-butyl (35,47?)-3-amino-4-fluoropyrrolidme-l -carboxylate (366 mg, 1.8 mmol) in dioxane (15 mL) was added (4R, 10b5)-2-benzyl- 8-bromo-4-methyl-l,2,3,4,6,l0b- hexahydropyrazino[2,l-a]isoindole (compound lj, 640 mg, 1.8 mmol,), Cs2C03 (1.7 g, 5.4 mmol) and XPhos Pd G2 (152 mg, 179 pmol). The reaction mixture was stirred at 85 °C overnight. The mixture was cooled to room temperature, diluted with water (50 mL) and extracted with EA (80 mL) for three times. The combined organic layer was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 40 g, 0% to 100% EtOAc in DCM) to afford compound 75a (710 mg, 82.5 % yield). MS: calc'd 481 [(M+H)+], measured 481 [(M+H)+] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; | 2.3 Step 3: preparation of (2R,6R)-4-(7-cyanopyrazolo[1,5-a]pyridin-4-yl)-N-[(3S,4R)-4- fluoropyrrolidin-3-yl]-6-methyl-morpholine-2-carboxamide (Example 2) To a solution of (2R,6R)-4-(7-cyanopyrazolo[1,5-a]pyridin-4-yl)-6-methyl-morpholine-2- carboxylic acid (compound 2b, 50 mg, 0.17 mmol), (3S,4R)-tert-butyl 3-amino-4- fluoropyrrolidine-1-carboxylate (CAS: 1174020-30-4, Pharmablock) (compound 2c, 54 mg, 0.26 mmol) and DPIEA (135 mg, 178 µL, 1.05 mmol) in DCM (3 mL) was added HATU (133 mg, 0.35 mmol). The mixture was stirred at rt overnight, then diluted with DCM, washed with sat. NH4Cl and brine, dried over Na2SO4, and concentrated to give a pale yellow oil. The oil was dissolved in DCM (2 mL), and cooled with ice water. To the solution was added TFA (0.5 mL). The mixture was warmed to rt, and stirred at rt for 1 h, then concentrated to give a crude product which was purified by prep-HPLC to give Example 2 (19 mg) as a white powder. (0204) 373 (MH+), measured 373 (MH+).1H NMR (400MHz, METHANOL-d4) 7.95 (d, J = 2.3 Hz, 1H), 7.39 (d, J = 7.9 Hz, 1H), 6.81 (d, J = 2.4 Hz, 1H), 6.54 (d, J = 7.9 Hz, 1H), 5.32 - 5.13 (m, 1H), 4.72 - 4.56 (m, 1H), 4.35 (dd, J = 2.8, 10.8 Hz, 1H), 4.01 (td, J = 2.2, 12.4 Hz, 1H), 3.98 - 3.89 (m, 1H), 3.69 - 3.56 (m, 3H), 3.53 - 3.46 (m, 1H), 3.32 (t, J = 11.2 Hz, 1H), 2.75 (dd, J = 10.9, 12.4 Hz, 1H), 2.63 (dd, J = 10.4, 12.5 Hz, 1H), 1.26 (d, J = 6.4 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 99.A Step A: Benzyl chlerefermate (708 mg, 592 pl_, 3.94 mmel) was added te a stirred selutien pf tert- butyl (3S,4R)-3-amino-4-fluoropyrrolidine-1-carboxylate (671 g, 0.1 melar, 3.29 mmel) and DIEA (1.14 ml_, 6.57 mmel) in dry DCM (33 ml_) at 0 °C. The mixture was allewed te warm te ream temperature evernight. The mixture was diluted with DCM, washed with 10% aqueeus petassium carbenate, dried ever sedium sulfate and cencentrated under reduced pressure tc give tert- butyl (3S,4R)-3-(((benzyloxy)carbonyl)amino)-4-fluoropyrrolidine-1-carboxylate (1.1 g, 99%). 1H NMR (400 MHz, CDCh) d 7.38 - 7.34 (m, 5H), 5.26 - 4.89 (m, 3H), 4.44 - 4.29 (m, 1 H), 3.98 - 3.42 (m, 3H), 3.19 - 3.04 (m, 1 H), 1.46 (s, 9H). |
99% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 99.A Step A: Benzyl chlerefermate (708 mg, 592 pl_, 3.94 mmel) was added te a stirred selutien pf tert- butyl (3S,4R)-3-amino-4-fluoropyrrolidine-1-carboxylate (671 g, 0.1 melar, 3.29 mmel) and DIEA (1.14 ml_, 6.57 mmel) in dry DCM (33 ml_) at 0 °C. The mixture was allewed te warm te ream temperature evernight. The mixture was diluted with DCM, washed with 10% aqueeus petassium carbenate, dried ever sedium sulfate and cencentrated under reduced pressure tc give tert- butyl (3S,4R)-3-(((benzyloxy)carbonyl)amino)-4-fluoropyrrolidine-1-carboxylate (1.1 g, 99%). 1H NMR (400 MHz, CDCh) d 7.38 - 7.34 (m, 5H), 5.26 - 4.89 (m, 3H), 4.44 - 4.29 (m, 1 H), 3.98 - 3.42 (m, 3H), 3.19 - 3.04 (m, 1 H), 1.46 (s, 9H). |
81% | With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 8.1 Step 1) cis-3-[(benzyloxy)carbonyl]amino}-4-fluoropyrrolidine-1-carboxylic acid tert-butyl ester To a solution of cis-3-amino-4-fluoropyrrolidine-1-carboxylic acid tert-butyl ester (0.3g, 1.47mmol) in dichloromethane (5mL) was added triethylamine (0.3mL, 2.14mmol), and then under nitrogen protection, cool to 0°C, and add benzyl chloroformate (0.25 mL, 1.76 mmol) dropwise. The mixture was slowly warmed to room temperature and stirred for 2 hours. After LC-MS showed that the reaction was complete, the reaction solution was poured into water (15 mL), extracted with ethyl acetate (15 mL x 3), and the organic layers were combined. The organic layer was saturated It was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (petroleum ether: ethyl acetate = 1:1) to obtain the title compound as a pale yellow oil (0.41 g, 81%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: Cs2CO3 / N,N-dimethyl-formamide / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: Cs2CO3 / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: hydrogen; palladium hydroxide on carbon / methanol / 2 h |
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