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CAS No. : | 90006-14-7 | MDL No. : | MFCD06662255 |
Formula : | C8H11BrClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BQCAANUXMMQVAY-UHFFFAOYSA-N |
M.W : | 236.54 | Pubchem ID : | 17174902 |
Synonyms : |
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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 |
---|---|---|
EXAMPLE 4 Since the lasalocid salt of R(+)-1-amino-1-(4-bromophenyl)-ethane had an optical purity of 100% after three crystallizations from methylene chloride/n-hexane (see Table 3), its conversion to the hydrochloride salt was undertaken. 1.58 grams (2 mmol) of the lasalocid salt of R(+)-1-amino-1-(4-bromophenyl)-ethane, isolated from the third crystallization from n-hexane, dissolved in 25 ml. of ethyl acetate were extracted twice with 25 ml. of 1N HCl. The aqueous extracts were combined and lyophilized to yield R(+)-1-amino-1-(4-bromophenyl)ethane hydrochloride, [α]D +2.6 (C 5, H2 O). The hydrochloride was optically pure (R) as determined by GLC of the N-trifluoracetyl-L-(S)-prolyl (TPC) derivative. Lasalocid was recovered quantitatively by evaporation of the ethyl acetate phase under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The (4-bromophenyl) acetylene (181 mg, 1.0 mmol), cat. [Au] (6 mg, 1 µM %), AgOTf (2.6 mg, 1 µM %), water (36 mg, 2 mmol) and methanol (1 ml) are added to the 25 mL of Claisen tube or. After closing the reaction at 120 C for 6 hours, cooling to room temperature. Then adding formic acid amine (315 mg, 5 mmol) and cat. [Rh] (6.2 mg, 1 mmol %), the reaction mixture in oil bath heated to 80 C, reaction 12 hours, cooling to room temperature. Rotary evaporation of the solvent and add a certain amount of ethyl acetate and water extraction, the organic phase of the resulting product after concentrated hydrochloric acid the reflux process, rotary evaporation to remove the solvent, the final petroleum ether washing and filtering to obtain the pure target compound, yield: 93% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.08% | With triethylamine; In isopropyl alcohol; at 80℃; for 12h; | A mixture of l-(4-bromophenyl)ethanamine (1 g, 4.23 m mol, 1 eq HC1), 4- chlorothieno[2,3-d]pyrimidine (794 mg, 4.65 mmol, 1.1 eq) and TEA (1.71 g, 16.91 mmol, 4 eq) in i-PrOH (20 mL) was stirred at 80C for 12 hours. The reaction was concentrated in vacuo. The residue was purified by column chromatography (SiCh, Petroleum (0532) ether/THF=30/l to 3/1) to give N-[l-(4-bromophenyl)ethyl]thieno[2,3-d]pyrimidin-4-amine (1.4 g, 4.19 mmol, 99.08% yield) as a white solid. (0533) [00250] (400MHz, CHLOROFORM-d) d 8.41 (s, 1H), 7.43 - 7.36 (m, 2H), (0534) 7.25 - 7.19 (m, 3H), 7.09 (d, J=6.0 Hz, 1H), 5.46 (quin, J=7.0 Hz, 1H), 5.28 (br d, J=7.1 Hz, 1H), 1.57 (d, J=6.8 Hz, 3H). ESI [M+H] = 334.2/336.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.49% | With triethylamine; In dichloromethane; at 0 - 25℃; for 12h; | To a solution of l-(4-bromophenyl)ethanamine (2 g, 8.46 mmol, 1.43 mL, 1 eq, HC1) in DCM (60 mL) was added TEA (2.57 g, 25.37 mmol, 3.53 mL, 3 eq ) and cooled to 0C with an ice bath, then B0C2O (2.21 g, 10.15 mmol, 2.33 mL, 1.2 eq) was added. The mixture was stirred at 0-25 C for 12 hrs. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=20/l to 3:1) to give tert-butyl N-[l-(4-bromophenyl)ethyl]carbamate (2.5 g, 8.33 mmol, 98.49% yield) as a white solid. (0665) [00311] ^ NMR (400 MHz, METHAN OL-d4) d 7.50 - 7.43 (m, 2H), 7.29 - 7.19 (m, 2H), 4.70 - 4.57 (m, 1H), 4.72 - 4.57 (m, 1H), 4.72 - 4.52 (m, 1H), 1.50 - 1.29 (m, 12H). ESI [M+H] = 285.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.09% | With triethylamine; In isopropyl alcohol; at 80℃; for 4h; | To a mixture of l-(4-bromophenyl)ethanamine (100 mg, 422.77 umol, 1 eq, HC1) and TEA (171 mg, 1.69 mmol, 4 eq ) in i-PrOH (2 mL) was added 4-chloroquinazoline (77 mg, 465.04 umol, 1.1 eq) and the mixture was stirred at 80C for 4 hours. The reaction was concentrated in vacuo. The residue was purified by column chromatography (S1O2, Petroleum ether/Ethyl acetate=10/l to 2:1) to give N-[l-(4-bromophenyl)ethyl]quinazolin-4- amine (250 mg, 761.72 umol, 90.09% yield, 2 batches in parallel) as a white solid. ESI (0406) [M+H] = 328.3/330.3. |
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