Glucokinase activator (gka) (R)-1

Base Information

Chemical Name:Glucokinase activator (gka) (R)-1
CAS No.:745051-65-4
Molecular Formula:C21H25N3O4S
Molecular Weight:415.513
Hs Code.:
UNII:W4S5EBH81C
Wikidata:Q27292293

Synonyms:Glucokinase activator (gka) (R)-1;W4S5EBH81C;Gka (R)-1;LY-2599506;UNII-W4S5EBH81C;745051-65-4;(R)-2-(4-(Cyclopropylsulfonyl)phenyl)-N-(pyrazin-2-yl)-3-(tetrahydro-2H-pyran-4-yl)propanamide;(R)-2-(4-(Cyclopropylsulfonyl)phenyl)-N-(pyrazin-2-yl)-3-(tetrahydropyran-4-yl)propionamide;SCHEMBL2651916;DQIITKNITDKAJZ-LJQANCHMSA-N;Q27292293;(2R)-2-(4-cyclopropanesulfonylphenyl)-N-pyrazin-2-yl-3-(tetrahydropyran-4-yl)propionamide

Suppliers and Price of Glucokinase activator (gka) (R)-1

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Glucokinase activator (gka) (R)-1

Chemical Property:

XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:415.15657746
Heavy Atom Count:29
Complexity:647

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:C1CC1S(=O)(=O)C2=CC=C(C=C2)C(CC3CCOCC3)C(=O)NC4=NC=CN=C4
Isomeric SMILES:C1CC1S(=O)(=O)C2=CC=C(C=C2)[C@@H](CC3CCOCC3)C(=O)NC4=NC=CN=C4
Recent EU Clinical Trials:A 12-Week, Phase 2, Randomized, Double-Blind, Active-Controlled Study of LY2599506 Given as Monotherapy or in Combination with Metformin in Patients with Type 2 Diabetes Mellitus

Technology Process of Glucokinase activator (gka) (R)-1

There total 22 articles about Glucokinase activator (gka) (R)-1 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:

: 5049-61-6
2-Aminopyrazine

: 745051-65-4
(R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(pyrazin-2-yl)-3-(tetrahydro-2H-pyran-4-yl)propanamide

Guidance literature:: (2R)-2-(4-cyclopropanesulfonyl-phenyl)-3-(tetrahydropyran-4-yl)-propionyl chloride; With pyridine; In dichloromethane; at -45 ℃; for 0.333333h;

2-Aminopyrazine; In tetrahydrofuran; dichloromethane; at -45 ℃; for 17.25h;

Reference yield:

: 5049-61-6
2-Aminopyrazine

: (2R)-2-(4-cyclopropanesulfonyl-phenyl)-3-(tetrahydropyran-4-yl)-propionyl chloride

: 745051-65-4
(R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(pyrazin-2-yl)-3-(tetrahydro-2H-pyran-4-yl)propanamide

Guidance literature:: With pyridine; In tetrahydrofuran; dichloromethane; at -45 ℃; Product distribution / selectivity;

Reference yield:

: 14633-54-6
cyclopropylphenylsulfide

: 745051-65-4
(R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(pyrazin-2-yl)-3-(tetrahydro-2H-pyran-4-yl)propanamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: aluminum (III) chloride / dichloromethane / 0 - 5 °C / Large scale reaction

1.2: 2 h / 0 - 5 °C / Large scale reaction

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / 0 - 20 °C / Large scale reaction

2.2: 0 - 20 °C / Large scale reaction

3.1: bis(norbornadiene)rhodium(l)tetrafluoroborate; (S_P,S′_P)-1,1′-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2′-bis[(R)-α-(dimethylamino)benzyl]ferrocene; hydrogen; triethylamine / methanol / 4 h / 20 °C / 4380.18 Torr / Inert atmosphere; Autoclave

4.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 20 - 30 °C / Large scale reaction

5.1: pyridine / tetrahydrofuran / 20 - 30 °C / Large scale reaction

With pyridine; bis(norbornadiene)rhodium(l)tetrafluoroborate; aluminum (III) chloride; oxalyl dichloride; (S_P,S′_P)-1,1′-bis[bis(4-methoxy-3,5-dimethylphenyl)phosphino]-2,2′-bis[(R)-α-(dimethylamino)benzyl]ferrocene; hydrogen; triethylamine; N,N-dimethyl-formamide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; 1.1: Friedel Crafts acylation / 1.2: Friedel Crafts acylation / 2.1: Wittig olefination / 2.2: Wittig olefination;
DOI:10.1021/op300053a