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Chemical Structure| 106092-09-5 Chemical Structure| 106092-09-5
Chemical Structure| 106092-09-5

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Product Details of Pramipexole Related Compound A

CAS No. :106092-09-5
Formula : C7H11N3S
M.W : 169.25
SMILES Code : NC1=NC2=C(S1)C[C@H](CC2)N
MDL No. :MFCD07368003
InChI Key :DRRYZHHKWSHHFT-BYPYZUCNSA-N
Pubchem ID :11521153

Safety of Pramipexole Related Compound A

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Pramipexole Related Compound A

* 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.

  • Downstream synthetic route of [ 106092-09-5 ]

[ 106092-09-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 106006-83-1 ]
  • [ 106092-11-9 ]
  • [ 106092-09-5 ]
YieldReaction ConditionsOperation 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.
  • 2
  • [ 599-91-7 ]
  • [ 106092-09-5 ]
  • [ 943319-02-6 ]
YieldReaction ConditionsOperation in experiment
88.2% With N-ethyl-N,N-diisopropylamine; In water; acetonitrile; at 76℃; for 6h; Add S-(-)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole (295.4 mmol, 50 g), acetonitrile 240 mL, stir, add purified water 10 mL, DIPEA (177.2 mmol, 22.9) g) n-propyl p-toluenesulfonate (472.6 mg, 101.3 g).After the addition, the reaction was stirred at 76°C for 6 hours and the reaction was completed.It was suction filtered and washed with acetonitrile.Drying gave 99.9 g of a white solid with a yield of 88.2percent.
64% In N,N-dimethyl-formamide; at 20℃; for 96h; Example 1; (S)-(-)-2-Amino-6-n-propylamino-4,5,6,7-tetrahydrobenzothiazole, p-toluenesulfonateThe suspension of (S)-(-)-2,6-diamino-4, 5,6,7- tetrahydrobenzothiazole (10 g, 0.06 mole) and n-propyl p- toluenesulfonate (38 g, 0.17 mole) in N,N-dimethylformamide (100 mL) was stirred at room temp, for 96 h. Pramipexole p-toluenesulfonate <n="8"/>was formed as creamy solid, which was washed with propan-2-ol. Yield of the product after drying: 14.2 g (64percent).M.p. 253-5°C (dec), *H NMR (DMSO-d6) delta: 7, 11-7,32 (2d, 4H), 3,50- 3,54 (m, IH), 3,06 (t, 2H), 2,81 (s, 3H), 1,96-3, 11 (s, 6H), 2,01 (m, 2H), 0,96 (t, 3H).
54% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; The p-toluenesulfonic acid salt of (S)-pramipexole 1 was prepared in 54percent yield, according to the literature,27 by reaction of diamine (S)-2 with n-<strong>[599-91-7]propyl tosylate</strong> 15, which was also prepared according to the literature.32 1H NMR (CD3OD): delta 7.72 (2H, d, J=8.0Hz, 2? and 6?), 7.25 (2H, d, J=8.0Hz, 3? and 5?), 3.55 (1H, dddd, J=11.6, 8.8, 5.3, 2.90Hz, 6-H), 3.09?3.05 (3H, m, 7a-H and CH2CH2CH3), 2.71?2.60 (3H, m, 4a-H, 4b-H and 7b-H), 2.39 (3H, s, PhCH3), 2.27 (1H, m, 5a-H), 1.93 (1H, dddd, J=12.9, 10.6, 9.6, 6.2Hz, 5b-H), 1.75 (2H, tq, J=8.0, 7.4Hz, CH2CH2CH3), 1.06 (3H, t, J=7.4Hz, CH2CH2CH3). (S)-Pramipexole p-toluenesulfonic salt (0.350 g, 0.914 mmol) was suspended in water (1.5 mL) and, after cooling at 0°C, 12 M hydrogen chloride aqueous solution (76 muL) was added. The mixture was kept under stirring for 15 min. after which 1 M sodium hydroxide aqueous solution (0.914 mL) was added while keeping the temperature at 0°C over 3 h. The precipitate pramipexole 1 was recovered by filtration and following the reported method,27 was transformed into the corresponding dihydrochloride monohydrate (0.245 g, 78percent).
  • 3
  • [ 72652-32-5 ]
  • [ 106092-09-5 ]
  • (S)-N-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-4-bromo-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% General procedure: A solution of (S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-amine(3) (1 mmol) and Na2CO3 (1 mmol) in DMF (10 ml) was stirred at room temperature for 15 min. 2,2,2-(Trichloroacetyl)pyrrole, <strong>[72652-32-5]1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone</strong> or 2,2,2-trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethanone (1.1 mmol) was added and mixture was stirred at 40 C for 2.5 h. Solvent was removed under reduced pressure and purified by column chromatography with dichloromethane/methanol (20:1) as an eluent.
 

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