Structure of 1031335-25-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1031335-25-7 |
Formula : | C10H20N2O2 |
M.W : | 200.28 |
SMILES Code : | O=C(OC(C)(C)C)N[C@@H]1C[C@H](N)CC1 |
MDL No. : | MFCD22394009 |
InChI Key : | PGBVMVTUWHCOHX-SFYZADRCSA-N |
Pubchem ID : | 51776940 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
In methanol; sodium hydroxide; | (8) cis-3-amino-1-(tert.-butyloxycarbonylamino)-cyclopentane Carried out with di-tert.butyl pyrocarbonate in the presence of 1N sodium hydroxide solution in methanol. Rf value: 0.63 (silica gel, methylene chloride/methanol/conc. aqueous ammonia=40:10:1) Mass spectrum (ESI+): m/z=201 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A slurry of 5 (6.45 g, 32.2 mmol) and NaBH(OAc)3 (10.92 g, 51.5 mmol) in dichloroethane (150 mL) was stirred 15 min. then treated with m-trifluoro- methoxybenzaldehyde (4.6 mL, 32.2 mmol) and additional dichloroethane (60 mL). After 4 h the reaction was quenched with water, the layers were separated and the aqueous layer was extracted with dichloromethane (2x). The combined organic layer was washed with brine and filtered through a cotton plug. Some solids were dissolved and rinsed through with sat. ammonia CHCI3 and solution was concentrated to an oil. Trituration provided 3.08 g of 6 as white solids and the filtrate was concentrated to 10.37 g of a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.1% | With hydrogen;nickel; In methanol; water; at 20 - 60℃; for 24h; | A mixture of 4 (48 g, 242 mmol) and Raney Ni 2800 (slurry in water, 30 g) in 400 mL of methanol was sealed under H2 (180 psi) at rt. The mixture then was heated to 60 0C and stirred at 60 C for 24 h. After cooling to rt, the mixture was filtered. The filtrate was concentrated to give a light yellow oil. Chromatography on Biotage 75 with 10% MeOH/DCM (0.5% NH4OH) gave 42.7 g (88.1 %) of 5 as waxy solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere; | To a solution of <strong>[1031335-25-7]tert-butyl N-[(1S)-3-aminocyclopentyl]carbamate</strong> (12.0 g, 59.9 mmol, 1.0 eq) and methyl 3-bromo-4-fluoro-benzoate (13.9 g, 59.9 mmol, 1.0 eq) in DMSO (150 mL) was added DIPEA (15.5 g, 119.8 mmol, 20.9 mL, 2.0 eq). The mixture was stirred at 120 C for 12 h, poured into H2O (250 mL) and extracted with EtOAc (80 mL*3). The combined organic layers were washed with brine (120 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2) to give compound 07-40-1 (16.0 g, 36.8 mmol, 61% yield). M+H+ = 413.2 (LCMS).1H NMR (CDCl3, 400 MHz): delta 8.12 (d, J = 1.88 Hz, 1H), 7.85 (dd, J = 8.60, 1.57 Hz, 1H), 6.58 (d, J = 8.66 Hz, 1H), 4.88 (br d, J = 4.64 Hz, 1H), 4.63 (br s, 1H), 4.09-3.99 (m, 1H), 3.86 (s, 3H), 2.62-2.51 (m, 1H), 2.15-2.04 (m, 2H), 1.75-1.63 (m, 2H), 1.45 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5% | With trifluoroacetic acid; In isopropyl alcohol; at 90℃; for 16h; | Into a 100-mL round-bottom flask, was placed 2-chloro-N-methylpyrimidin-4-amine (300 mg, 2.09 mmol, 1 equiv), trifluoroacetic acid (2.375 g, 21.01 mmol, 10.06 equiv), IPA (5 mL), <strong>[1031335-25-7]tert-butyl N-[(1S,3R)-3-aminocyclopentyl]carbamate</strong> (459 mg, 2.29 mmol, 1.10 equiv). The resulting solution was stirred for 16 h at 90 C in an oil bath. The crude product was purified by Prep-HPLC C TFA. This resulted in 33.2 mg (5%) of N2-((1R,3S)-3-aminocyclopentyl)-N4-methylpyrimidine-2,4-diamine as light yellow oil. |