(6S,7R)-N6-propyl-N7-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine

Base Information

• Chemical Name: (6S,7R)-N6-propyl-N7-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine
• CAS No.: 1244656-98-1
• Molecular Formula: C₂₀H₃₂N₆S₂
• Molecular Weight: 420.646
• Mol file: 1244656-98-1.mol

Synonyms:

Chemical Property of (6S,7R)-N6-propyl-N7-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine

Chemical Property:

• Boiling Point: 628.7±65.0 °C(Predicted)
• Density: 1.26±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

(6S,7R)-4,5,6,7-Tetrahydro-N6-propyl-N7-[(6S)-4,5,6,7-tetrahydro-6-(propylamino)-2-benzothiazolyl]-2,6,7-benzothiazoletriamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Pramipexole Dimer Impurity is derived from Pramipexole (P700750). Antiparkinsonian. Pramipexole (Mirapex, Mirapexin, Sifrol) is a non-ergoline dopamine agonist indicated for treating early-stage Parkinson''s disease (PD) and restless legs syndrome (RLS).[1] It is also sometimes used off-label as a treatment for cluster headache and to counteract the problems with sexual dysfunction experienced by some users of the selective serotonin reuptake inhibitor (SSRI) antidepressants.

Technology Process of (6S,7R)-N6-propyl-N7-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine

There total 13 articles about (6S,7R)-N6-propyl-N7-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine 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:

(6S,7R)-N7-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine + propionaldehyde (123-38-6) → (6S,7R)-N6-propyl-N7-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine (1244656-98-1)

Guidance literature:

(6S,7R)-N₇-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine; propionaldehyde; In methanol; at -20 ℃; for 0.75h;

With sodium tetrahydroborate; In methanol; at -20 - 20 ℃; for 4.5h;

DOI:10.1021/acs.oprd.6b00182

Reference yield:

(S)-tert-butyl (2-((tert-Butoxycarbonyl)amino)-4,5,6,7-tetrahydrobenzothiazol-6-yl)(propyl)carbamate → (6S,7R)-N6-propyl-N7-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine (1244656-98-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

2.1: hydrogenchloride; water / 95 °C

3.1: methanol / 0.75 h / -20 °C

3.2: 4.5 h / -20 - 20 °C

With hydrogenchloride; di-isopropyl azodicarboxylate; water; triphenylphosphine; In tetrahydrofuran; methanol; 1.1: |Mitsunobu Displacement;

DOI:10.1021/acs.oprd.6b00182

Reference yield:

pramipexole (104632-26-0) → (6S,7R)-N6-propyl-N7-((S)-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazol-2-yl)-4,5,6,7-tetrahydrobenzothiazole-2,6,7-triamine (1244656-98-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 0 - 35 °C

2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

3.1: hydrogenchloride; water / 95 °C

4.1: methanol / 0.75 h / -20 °C

4.2: 4.5 h / -20 - 20 °C

With hydrogenchloride; di-isopropyl azodicarboxylate; water; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2.1: |Mitsunobu Displacement;

DOI:10.1021/acs.oprd.6b00182

upstream raw materials:

propionaldehyde

pramipexole

(6S,7S)-2,6-diamino-7-hydroxy-4,5,6,7-tetrahydrobenzothiazole D-tartrate salt

(6S,7S)-2,6-diamino-7-hydroxy-4,5,6,7-tetrahydrobenzothiazole

Refernces