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CAS No. : | 106092-11-9 | MDL No. : | MFCD07369986 |
Formula : | C7H11N3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DRRYZHHKWSHHFT-SCSAIBSYSA-N |
M.W : | 169.25 | Pubchem ID : | 16743100 |
Synonyms : |
|
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: |
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* 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 |
---|---|---|
Resolution of racemate;Purification / work up; | Example 4; Preparation of 2-amino-6-(alkyl)amino-4,5,6,7-tetrahydrobenzothiazole Compounds of Formulas (9a) and (9b)Under Polar Organic Conditions on a Chiralpak AD Column; [0066] The resolution of the compound of formula (9) was completed asfollows. A sample solution was prepared by dissolving 100 mg of a compound offormula (9) in 100 mL of ACN with 0.2percent DBA. The sample solution was loadedonto the Chiralpak AD column (50 mm x 500 mm) using ACN with 0.2percent DEA asmobile phase. The first enantiomer was observed from 38-50 minutes while thesecond one eluted from 91-110 minutes. Both components were collected andconcentrated to dryness using a rotary evaporator with a bath temperature of 30-35°C. The recovered material was dried under vacuum for at least 12 h to removeresidual solvents.Example 5 Preparation of 2-amino-6-(alkyl)amino-4,5,6,7-tetrahydrobenzothiazole Compounds of Formulas (9a) and (9b)Under Polar Organic Conditions on a Chiralpak AD Column[0067] The resolution of the compound of formula (9) was completed asfollows. A sample solution was prepared by dissolving 100 mg of a compound offormula (9) in 100 mL of 5:95 IPA/ACN with 0.2percent DEA. The sample solutionwas loaded onto the Chiralpak AD column (50 mm x 500 mm) using 5:95IPA/ACN with 0.2percent DEA as mobile phase. The first component of the mixturewas observed from 28-35 minutes while the second one eluted from 56-70minutes. Both components were collected upon elution and processed asdescribed above. These conditions are preferred for the resolution of large scalebatches.Example 6 Preparation of Chirally Pure 2-amino-6-(alkyl)amino-4,5,6,7-tetrahydrobenzothiazole Compounds of Formulas (9a) and (9b)Under Polar Organic Conditions on a Chiralpak AD Column[0068] The resolution of the compound of formula (9) was completed asfollows. A sample solution was prepared by dissolving 100 mg of a compound offormula (9) in 100 mL of 10:90 IPA/ACN with 0.2percent DBA. The sample solutionwas loaded onto the Chiralpak AD column (50 mm x 500 mm) using 10:90IP A/ACN with 0.2percent DEA as mobile phase. The first enantiomer was observedfrom 13-18 minutes while the second one eluted from 20-30 minutes. Bothcomponents were collected and processed as described previously.[0069] Samples of the resolved material from Examples 4-6 (1 mg each)were dissolved at 1 mg/mL in ACN and analyzed by HPLC. The chiral purity ofboth fractions was greater than 99percent, while the weight recovery was greater than90percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 65℃; for 7h;Product distribution / selectivity; | [00250) EXAMPLE 7 - Preparation of (R)-pramipexole p-TSA salt: Condition C:A 12 L, three necked flask was equipped with an overhead stirrer, a temperature probe, a heating mantle, a claisen joint, a condenser, and a 500 ml addition funnel. The flask was charged with 250 grams of R(+)-2,6 diamino-4,5,6,7-tetrahydro-benzothiazole (R(+) diamine), followed by 2 L of dimethyl formamide (DMF). Under continuous stirring, the mixture was heated to a temperature of 65C. The addition funnel was charged with a solution of 386.6 grams <strong>[599-91-7]propyl tosylate</strong> (1.25 molar equivalents) and 322 ml diisopropylethyleamine (1.25 molar equivalents) in 500 ml DMF. This solution was added to the 12 L flask dropwise over a period of 2.0 hours. The reaction was monitored by analysis on HPLC.[00251] The reaction was continued at 65C for an additional 5 hours, after which the solution was gradually cooled to room temperature and stirred overnight. The solution was diluted with 2 L MTBE and stirred for an additional 0.5 hours. The precipitated material was collected by filtration and washed with 500 ml MTBE, followed by 3 washes of 500 ml each reagent alcohol. The washed precipitated cake was dried under high vacuum.[00252] The final weight of the dried product was 317.6 grams, representing a 56percent yield. HPLC was used to determine the chemical purity of the R(+)-2,6-diamino-4,5,6,7- tetrahydro-benzothiazole ((S)-pramipexole) as 98.4percent and the chiral purity as greater than 99.8percent. 1H NMR and 13C NMR was used to confirm the structure: 1H NMR (300 MHz, DMSO-rf6) delta 8.5 (br.s, 2H), 7.5 (d, 2H), 71.2 (d, 1H), 6.8 (s, 2H), 3.4 (m, 1H), 2.95 (m, 3H), 2.6 (m, 2H, merged with DMSO peak), 2.3 (s, 3H), 2.15 (m, 1H), 1.8 (m, I H), 1.55 (m, 2H), 0.9 (t, 3H); 13C NMR (300 MHz, DMSO-6) delta 167.0, 145.5, 144.6, 138.4, 128.6, 125.8, 1 10.7, 53.9, 46.5, 25.8, 25.6, 24.5, 21.2, 19.6, 1 1.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.9% | With N-ethyl-N,N-diisopropylamine; In water; acetonitrile; at 20 - 80℃;Inert atmosphere; | Example 1 : (R)-(+)-2-amino-4,5,6,7-tetrahvdro-6-(n- [00132] Method 1: [00133] Compound 2 (100 g, 590.9 mmol, 98.8percent ee) was charged in a 1 L reactor equipped with nitrogen inlet, condenser, thermometer and overhead stirrer at room temperature. Acetonitrile (487.5 mL, 4.875 Volumes) was added to the reactor and agitation was started. Water (12.5 mL, 0.125 Volumes) was then added to the reactor, followed by DIPEA (38.2 g, 295 mmol). n-Propyl p-toluenesulfonate (189.9 g, 886 mmol) was then added to the reactor and the reaction mixture was heated to about 75 to 80 °C with stirring. The reaction stirred at about 75 to 80 °C for 6-16 hours, until complete (typically about 8-10 hours). The batch was then cooled to room temperature over 2-3 hours and aged at room temperature for additional 1 hour. The reaction mixture was filtered at room temperature, and the wet cake was washed with acetonitrile (250 mL) twice and dried to a constant weight to provide the product in 83.9percent yield (190.1 g), 98.2percent purity (determined by achiral HPLC), and about 100percent ee. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | The resulting solids were dried under high vacuum for 2 h and then taken up in 50 mL of ethanol and cooled to between 0 and 5° C. With continuous stirring, concentrated HCl (45 mL) was slowly added to the reaction while maintaining the temperature at between 0 and 5° C., and the mixture was stirred for an additional 15 min. Methyl t-butyl ether (MTBE, 270 mL) was added to mixture, and stirring was continued for additional 1.5 h at this temperature. The mixture was filtered, washed twice with an MTBE/ethanol solution (2:1; 2*70 mL), and dried under high vacuum at room temperature for 18 h to afford 38.5 g of the di-hydrochloride salt of (R)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine (Yield: 51percent). MS calculated for C10H17N3S: 211.11. found: 212.1 [M+H]+. |
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