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Structure of 37493-16-6
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 37493-16-6 |
Formula : | C3H7ClO |
M.W : | 94.54 |
SMILES Code : | C[C@H](O)CCl |
MDL No. : | MFCD01862133 |
InChI Key : | YYTSGNJTASLUOY-VKHMYHEASA-N |
Pubchem ID : | 641044 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225-H302-H315-H319-H335 |
Precautionary Statements: | P210-P261-P305+P351+P338 |
Class: | 3 |
UN#: | 1993 |
Packing Group: | Ⅲ |
* 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 hydrogenchloride; water; lithium chloride; In tetrahydrofuran; at -30 - 20℃; for 20h; | Example 4A; (2S)-1-Chloropropan-2-ol 32.50 g (766.66 mmol) of lithium chloride are initially charged in 100 ml of THF. 18.75 ml (92.97 mmol) of 4.96 M hydrochloric acid are then added. The mixture is cooled to -30 C., and a solution of 5.40 g (92.97 mmol) of S-(-)-propylene oxide in 10 ml of THF is added dropwise. After the addition, the mixture is warmed to RT and stirred for 20 h. The precipitate formed is filtered off with suction, and the filtrate is subjected to fractional distillation (61 mbar, 30-40 C. head temperature). The product mixture obtained in this manner is used without further purification in the subsequent step.Yield: 4.50 g (16% of theory, 32% purity)1H-NMR (400 MHz, DMSO-d6): δ=5.01 (d, 1H), 3.85-3.74 (m, 1H), 3.49 (d, 2H), 1.12 (d, 3H).The product contains about 10% of the regioisomer (2S)-2-chloropropan-1-ol:1H-NMR (400 MHz, DMSO-d6): δ=5.18-5.12 (m, 1H), 4.11-4.03 (m, 1H), 3.49 (d, 2H), 1.41 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.8% | With hydrogenchloride; at 40℃; | In a 1000 mL reaction flask, 378 g (4 mol) of (S) -1-chloro-2-propanol, 144 g (4.8 mol) of paraformaldehyde,Stirring into a suspension, slowly into the dry HCl gas, controlling the temperature does not exceed 40 ,Until the solid was dissolved in the reaction solution was transferred to a separatory funnel, the lower organic phase was separated, dried over anhydrous sodium sulfate,The desiccant was filtered off and distilled under reduced pressure to give 433.8 g of a colorless liquid, yield 75.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With potassium carbonate; In acetonitrile; at 85℃; for 96h; | Add acetonitrile (45 mL) to a mixture of 5-rnethyi-3-nitro-IH-pyrazoie (1.2 g, 9.0 rnmoi). potassium carbonate (2.5 g, 2.0 eq). and (S)-1-chloro-2-propanol (().98 g, 1.2 eq). Stir at 85 C for four days. Cool to a Filter to collect the solid and rinse the solid with EtOAc, then discard the solid. Collect and concentrate the filtrate n vacuo to provide aresidue. Subject the residue to normal phase chromatography, eluting with 50% EtOAc in hexanes. to give the title compound as a white solid (1.1 g, 67%). MS (ES) m/z 186 (4+H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In water; at 70℃; for 24h; | General procedure: Pure enantiomers (R)- and (S)-proxyphylline were synthesized asfollows: 1 equiv theophylline and 1.15 equiv of potassium hydroxidewere dissolved at 70C in water. 1.15 equiv of (R)- or <strong>[37493-16-6](S)-1-chloro-2-propanol</strong> mixed with water was then added dropwise, and thereaction mixture was stirred over 24 h at 70C. The water wasevaporated under vacuum, and the solid was dried. The solid wasdissolved in EtOH, and heated for 3 h and filtered. After evaporatingEtOH, the crude product was purified by HPLC (YMC-Pack ODSAL250×20) with acetonitrile-H2O (1 : 9) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dimethyl sulfoxide; at 100℃; for 16h; | To a well stirred solution of 3-(2-cyclopropyl-1H-imidazol-1-yl)phenol (1 molar equiv.) in DMSO (0.3 M) were added (S)-l-chloropropan-2-ol (2 molar equiv.) and K2C03 (3 molar equiv.). The reaction mixture was heated at 100 C for 16 hours. The reaction mixture was cooled and poured in to water and extracted with EtOAc. The combined organic layer was washed with water and brine, dried over Na2S04 and concentrated under reduced pressure. The crude product was purified by column chromatography to afford (S)-1-(3-(2-cyclopropyl-1H-imidazol-1-yl)phenoxy)propan-2-ol. 1H NMR (400 MHz, CDC13) δ (ppm): 7.41-7.36 (m, 1H), 7.02 (t, = 8.0 Hz, 4H), 4.25-4.20 (m, 1H), 3.97 (dd, = 4.0, 12.0 Hz, 1H), 3.85 (t, = 8.0 Hz, 1H), 2.34 (s, 1H), 1.82-1.75 (m, 1H), 1.30 (d, = 4.0 Hz, 3H), 1.12-1.09 (m, 2H), 0.92-0.87 (m, 2H); MS (ESI) m/z 259.21 [Ci5H18N202+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 18h; | To a mixture of 6-bromo-3-(l-hydroxy-2-methylpropan-2-yl)-l,3-dihydro-2iT- imidazo[4,5-Z>]pyridin-2-one (100 mg, 0.349 mmol) and (ri)-l-chloropropan-2-ol (49.6 mg, 0.524 mmol) in DMF (3 mL) was added K2CO3 (97 mg, 0.699 mmol). The reaction mixture was stirred at 90C for 18 hours, then cooled to RT, diluted with EtOAc and washed with brine. The organic phase was dried over Na2S04, filtered and concentrated to give the title compound (120 mg, 100%) which was used without further purification. ESI-MS m/z [M+H]+ = 344.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.2 g | With pyridine; In N,N-dimethyl-formamide; at 20℃; | To a solution of (S)-(+)-1-chloropropan-2-ol (1 .0 g, 10.6 mmol) in N,N-dimethylformamide (20 ml_) at 20 C was added pyridine (1.0 g, 12.7 mmol) and fe/ -butyldimethylsilyl chloride (1.91 g, 12.7 mmol). After stirring for 20 C, the reaction was diluted with water (40 ml_). The resulting mixture was extracted with methyl te/ -butyl ether (2 x 40 ml_). The organic extracts were combined, washed with brine (50 ml_), and dried (Na2S04). The solvent was removed to give the title compound (2.2 g), which was used without further purification. 1H NMR (400 MHz, CDCI3) d 3.96 (m, 1 H), 3.42 (dd, J = 10.8, 5.9 Hz, 1 H), 3.34 (dd, J = 10.7, 5.9 Hz, 1 H), 1.23 (d, J = 6.1 Hz, 3H), 0.89 (s, 9H), 0.08 (d, J = 4.1 Hz, 6H). |
2.2 g | With pyridine; In N,N-dimethyl-formamide; at 20℃; | To a solution of (S)-(+)-1-chloropropan-2-ol (1 .0 g, 10.6 mmol) in N,N-dimethylformamide (20 ml_) at 20 C was added pyridine (1.0 g, 12.7 mmol) and fe/ -butyldimethylsilyl chloride (1.91 g, 12.7 mmol). After stirring for 20 C, the reaction was diluted with water (40 ml_). The resulting mixture was extracted with methyl te/ -butyl ether (2 x 40 ml_). The organic extracts were combined, washed with brine (50 ml_), and dried (Na2S04). The solvent was removed to give the title compound (2.2 g), which was used without further purification. 1H NMR (400 MHz, CDCI3) d 3.96 (m, 1 H), 3.42 (dd, J = 10.8, 5.9 Hz, 1 H), 3.34 (dd, J = 10.7, 5.9 Hz, 1 H), 1.23 (d, J = 6.1 Hz, 3H), 0.89 (s, 9H), 0.08 (d, J = 4.1 Hz, 6H). |