GPi 688

Base Information

• Chemical Name: GPi 688
• CAS No.: 918902-32-6
• Molecular Formula: C₁₉H₁₈ClN₃O₄S
• Molecular Weight: 419.889
• Mol file: 918902-32-6.mol

Synonyms:GPi 688

Chemical Property of GPi 688

Chemical Property:

• Boiling Point: 885.9±65.0 °C (760 mmHg)
• PSA: 133.90000
• Density: 1.59±0.1 g/cm3 (20 °C, 760 mmHg)
• LogP: 2.37960

Purity/Quality:

≥99% by HPLC ^*data from raw suppliers

GPi688 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: GPi 688 is a allosteric glycogen phosphorylase inhibitor; acts at the indole site of glycogen phosphorylase. Inhibits glucagon-mediated hyperglycemia in vivo in the rat.

Technology Process of GPi 688

There total 47 articles about GPi 688 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: 83.0%

N-{1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide → 2-chloro-N-[1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide (918902-32-6)

Guidance literature:

N-{1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide; With hydrogenchloride; water; In tetrahydrofuran; for 4h;

With triethylamine; In tetrahydrofuran;

Reference yield:

Cbz-D-Phe (2448-45-5) → 2-chloro-N-[1-((2S)-2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-(3R)-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide (918902-32-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Et₃N; EDAC; HOBt / dimethylformamide / 20 °C

2.1: TFA; (CF₃CO₂)2IPh / CH₂Cl₂ / 0 °C

3.1: H₂ / Pd/C / ethyl acetate / 750.06 Torr

4.1: aq. HCl; H₂ / Pd/C / ethanol / 25 °C / 2250.18 Torr / pH 3

5.1: Et₃N / CH₂Cl₂ / 20 °C

6.1: NaH / dimethylformamide / 0.33 h / 0 °C

6.2: dimethylformamide / 0 - 20 °C

7.1: HCl / dioxane / 20 °C

8.1: HOBt; EDAC; Et₃N / dimethylformamide / 20 °C / pH 8

With hydrogenchloride; hydrogen; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.10.037

Reference yield:

Cbz-D-Phe (2448-45-5) → 2-chloro-{(3R)-1-[(2R)-2,3-dihydroxypropyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide (918902-32-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Et₃N; EDAC; HOBt / dimethylformamide / 20 °C

2.1: TFA; (CF₃CO₂)2IPh / CH₂Cl₂ / 0 °C

3.1: H₂ / Pd/C / ethyl acetate / 750.06 Torr

4.1: aq. HCl; H₂ / Pd/C / ethanol / 25 °C / 2250.18 Torr / pH 3

5.1: Et₃N / CH₂Cl₂ / 20 °C

6.1: NaH / dimethylformamide / 0.33 h / 0 °C

6.2: dimethylformamide / 0 - 20 °C

7.1: HCl / dioxane / 20 °C

8.1: HOBt; EDAC; Et₃N / dimethylformamide / 20 °C / pH 8

With hydrogenchloride; hydrogen; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.10.037

upstream raw materials:

2-Chloro-6H-thieno[2,3-b]pyrrole-5-carboxylic acid

benzyl (S)-(1-(methoxyamino)-1-oxo-3-phenylpropan-2-yl)carbamate

N-Cbz-L-Phe

Cbz-D-Phe