(R)-4,5,6,7-Tetrahydro-benzothiazole-2,6-diamine

Base Information

• Chemical Name: (R)-4,5,6,7-Tetrahydro-benzothiazole-2,6-diamine
• CAS No.: 106092-11-9
• Molecular Formula: C7H11N3S
• Molecular Weight: 169.25
• Hs Code.: 29341000
• European Community (EC) Number: 690-698-9
• ChEMBL ID: CHEMBL1190822
• DSSTox Substance ID: DTXSID80587748
• Wikidata: Q72463096
• Mol file: 106092-11-9.mol

Synonyms:106092-11-9;(R)-4,5,6,7-Tetrahydro-benzothiazole-2,6-diamine;(r)-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine;(6R)-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;(+)-(6R)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole;(R)-N-Despropyl Pramipexole;MFCD07369986;2,6-Benzothiazolediamine, 4,5,6,7-tetrahydro-, (R)-;SCHEMBL2051128;CHEMBL1190822;DTXSID80587748;DRRYZHHKWSHHFT-SCSAIBSYSA-N;BCP28311;AKOS015915313;CS-W019104;DS-0449;112GI016;AC-20378;A13054;EN300-624156;(6R)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole;(6R)-2,6 diamino-4,5,6,7-tetrahydro-benzothiazole;(R)-(+)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole;R-(+)-2,6-Diamino-4,5,6,7- tetrahydrobenzothiazole;(+)-(R)-4,5,6,7-Tetrahydro-benzothiazole-2,6-diamine;(6R)-4,5,6,7-Tetrahydro-2,6-benzothiazolediamine;(R)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole;(R)-4,5,6,7-Tetrahydrobenzothiazole-2,6-diamine

Chemical Property of (R)-4,5,6,7-Tetrahydro-benzothiazole-2,6-diamine

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 2.45E-05mmHg at 25°C
• Melting Point: 228-230 °C
• Refractive Index: 1.655
• Boiling Point: 359 °C at 760 mmHg
• PKA: 9.18±0.20(Predicted)
• Flash Point: 170.9 °C
• PSA: 93.17000
• Density: 1.313 g/cm³
• LogP: 1.82280
• Storage Temp.: Refrigerator
• Solubility.: Methanol (Sparingly), Water (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 169.06736854
• Heavy Atom Count: 11
• Complexity: 153

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-N-DespropylPramipexole ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(CC1N)SC(=N2)N
• Isomeric SMILES: C1CC2=C(C[C@@H]1N)SC(=N2)N
• Uses: (R)-Pramipexole intermediate as dopamine autoreceptor agonist. (R)-Pramipexole (P700745) intermediate as dopamine autoreceptor agonist.

Technology Process of (R)-4,5,6,7-Tetrahydro-benzothiazole-2,6-diamine

There total 5 articles about (R)-4,5,6,7-Tetrahydro-benzothiazole-2,6-diamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.5%

2,6-diamino-4,5,6,7-tetrahydro-benzthiazole (106006-83-1,104617-49-4) → (R)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine (106092-11-9,104617-49-4)

Guidance literature:

With D-tartaric acid; In ethanol; at 80 ℃; for 3h;

DOI:10.1021/acs.jmedchem.5b00489

Reference yield:

2,6-diamino-4,5,6,7-tetrahydro-benzthiazole (106006-83-1,104617-49-4) → (R)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine (106092-11-9,104617-49-4) + (S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-diamine (106092-09-5,104617-49-4)

Guidance literature:

optical resolution with chiral tartaric acid;

DOI:10.1016/j.bmcl.2004.03.085

Reference yield:

N-(4-oxocyclohexyl)acetamide (27514-08-5) → (R)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine (106092-11-9,104617-49-4)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid; bromine / 4 h / 60 °C

2: 60 °C / Reflux

3: hydrogen bromide / Reflux

4: D-tartaric acid / ethanol / 3 h / 80 °C

With D-tartaric acid; hydrogen bromide; bromine; acetic acid; In ethanol;

DOI:10.1021/acs.jmedchem.5b00489

upstream raw materials:

2,6-diamino-4,5,6,7-tetrahydro-benzthiazole

N-(4-oxocyclohexyl)acetamide

2-bromo-4-acetamidocyclohexanone

N-(2-amino-4,5,6,7-tetrahydrobenzo[1,2-d]thiazol-6-yl)acetamide

Downstream raw materials:

(R)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride

(R)-(+)-2-amino-4,5,6,7-tetrahydro-6-(n-propylamino)benzothiazole p-toluenesulfonic acid

(R)-(+)-pramipexole

(+)-2-amino-6-propionamidotetrahydrobenzothiazole

Refernces

• 1、 -. "PROCESS FOR PREPARING CHIRALLY PURE 2-AMINO-6-(ALKYL)AMINO-4,5,6,7-TETRAHYDROBENZOTHIAZOLES BY LIQUID CHROMATOGRAPHIC RESOLUTION". Page/Page column 16-17. . Retrieved 2008/06/13.
• 2、 Schneider, Claus S.,Mierau, Joachim. "Dopamine autoreceptor agonists: Resolution and pharmacological activity of 2,6-diaminotetrahydrobenzothiazole and an aminothiazole analogue of apomorphine". . p. 494 - 498. Retrieved 2007/10/02.