(1S,2R,3S,4R)-4-[7-[[(2R)-1-(3-chlorothiophen-2-yl)butan-2-yl]amino]imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentane-1-carboxamide

Base Information

Chemical Name:(1S,2R,3S,4R)-4-[7-[[(2R)-1-(3-chlorothiophen-2-yl)butan-2-yl]amino]imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentane-1-carboxamide
CAS No.:143395-98-6
Molecular Formula:C₂₂H₂₈ClN₅O₃S
Molecular Weight:478.015
Hs Code.:
UNII:85CCL08543
Pharos Ligand ID:K7YBAM9J64ZW
ChEMBL ID:CHEMBL1950650
Mol file:143395-98-6.mol

(1S,2R,3S,4R)-4-[7-[[(2R)-1-(3-chlorothiophen-2-yl)butan-2-yl]amino]imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentane-1-carboxamide

Synonyms:143395-98-6;CHEMBL1950650;85CCL08543;RPR-100579;(1S,2R,3S,4R)-4-[7-[[(2R)-1-(3-chlorothiophen-2-yl)butan-2-yl]amino]imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentane-1-carboxamide;4-(7-(((1R)-1-((3-Chloro-2-thienyl)methyl)propyl)amino)-3H-imidazo(4,5-b)pyridin-3-yl)-N-ethyl-2,3-dihydroxycyclopentanecarboxamide, (1S,2R,3S,4R)-;Cyclopentanecarboxamide, 4-(7-(((1R)-1-((3-chloro-2-thienyl)methyl)propyl)amino)-3H-imidazo(4,5-b)pyridin-3-yl)-N-ethyl-2,3-dihydroxy-, (1S,2R,3S,4R)-;Cyclopentanecarboxamide, 4-[7-[[(1R)-1-[(3-chloro-2-thienyl)methyl]propyl]amino]-3H-imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxy-, (1S,2R,3S,4R)-;D0QH7H;SCHEMBL3066730;UNII-85CCL08543;DNPNXAXAKNFJDD-GFOALDQYSA-N;BDBM50364064;AKOS040747811;PD160992;(1s,2r,3s,4r)-4-[7-[1(r)-(3-chloro-2-thienylmethyl)propylamino]-3h-imidazo[4,5-b]pyridin-3-yl]-n-ethyl-2,3-dihydroxycyclopentane-1-carboxamide;CYCLOPENTANECARBOXAMIDE, 4-(7-((1-((3-CHLORO-2-THIENYL)METHYL)PROPYL)AMINO)-3H-IMIDAZO(4,5-B)PYRIDIN-3-YL)-N-ETHYL-2,3-DIHYDROXY-, (1S-(1.ALPHA.,2.BETA.,3.BETA.,4.ALPHA.(S*)));Cyclopentanecarboxamide, 4-(7-((1-((3-chloro-2-thienyl)methyl)propyl)amino)-3H-imidazo(4,5-b)pyridin-3-yl)-N-ethyl-2,3-dihydroxy-, (1S-(1alpha,2beta,3beta,4alpha(S*)))

Suppliers and Price of (1S,2R,3S,4R)-4-[7-[[(2R)-1-(3-chlorothiophen-2-yl)butan-2-yl]amino]imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentane-1-carboxamide

Supply Marketing:

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

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Total 2 raw suppliers

Chemical Property of (1S,2R,3S,4R)-4-[7-[[(2R)-1-(3-chlorothiophen-2-yl)butan-2-yl]amino]imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentane-1-carboxamide

Chemical Property:

XLogP3:3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:8
Exact Mass:477.1601386
Heavy Atom Count:32
Complexity:649

Purity/Quality:: 97% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CCC(CC1=C(C=CS1)Cl)NC2=C3C(=NC=C2)N(C=N3)C4CC(C(C4O)O)C(=O)NCC
Isomeric SMILES:CC[C@H](CC1=C(C=CS1)Cl)NC2=C3C(=NC=C2)N(C=N3)[C@@H]4C[C@@H]([C@H]([C@H]4O)O)C(=O)NCC

Technology Process of (1S,2R,3S,4R)-4-[7-[[(2R)-1-(3-chlorothiophen-2-yl)butan-2-yl]amino]imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentane-1-carboxamide

There total 9 articles about (1S,2R,3S,4R)-4-[7-[[(2R)-1-(3-chlorothiophen-2-yl)butan-2-yl]amino]imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentane-1-carboxamide 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: 75.0%

: 313268-74-5
[3aR-[3aα,4α,6a(R*),6aα]]-6-[7-[[1-[(3-chlorothien-2-yl)methyl]propyl]amino]-3H-imidazo(4,5-b)pyrid-3-yl] N-ethyl tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide

: 143395-98-6
[1S-[1α,2β,3β,4α(S*)]]-4-[7-[[1-[(3-chlorothien-2-yl)methyl]propyl]amino]-3H-imidazo[4,5-b]pyrid-3-yl] N-ethyl 2,3-dihydroxycyclopentanecarboxamide

Guidance literature:: [3aR-[3aα,4α,6a(R*),6aα]]-6-[7-[[1-[(3-chlorothien-2-yl)methyl]propyl]amino]-3H-imidazo(4,5-b)pyrid-3-yl] N-ethyl tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide; With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 3h;

With sodium carbonate; at 20 ℃; for 16h; Further stages.;
DOI:10.1021/jo001066f

Reference yield:

: methane sulfonic acid

[3aR-[3aa,4a,6a(R*),6aa]]-6-[7-[[1-[(3-chlorothien-2-yl)methyl]propyl][4-methylbenzenesulfonyl]aminio]-3H-imidazo]4,5-b]pyrid-3-yl]N-ethyl tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide: [3aR-[3aa,4a,6a(R*),6aa]]-6-[7-[[1-[(3-chlorothien-2-yl)methyl]propyl][4-methylbenzenesulfonyl]aminio]-3H-imidazo]4,5-b]pyrid-3-yl]N-ethyl tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide

: [3aR-[3aα,4α,6a(R*),6aα]]-6-[7-[[1-[(3-chlorothien-2-yl)methyl]propyl][4-methylbenzenesulfonyl]amino]-3H-imidazo[4,5-b]pyrid-3-yl]N-ethyl tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide

: 1634-04-4
tert-butyl methyl ether

: 100-68-5
methyl-phenyl-thioether

: 193417-93-5,143395-98-6
[1S-[1a,2b,3b,4a]]-4-[7-[[2-(3-chloro-2-thienyl)-1-ethylethyl]amino]-3H-imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentane-carboxamide

Guidance literature:: With hydrogenchloride; methanesulfonic acid; In acetic acid butyl ester; water; ethyl acetate; toluene; trifluoroacetic acid;

Reference yield:

: 5975-12-2
2,4-dichloro-3-nitro-pyridine

: 143395-98-6
[1S-[1α,2β,3β,4α(S*)]]-4-[7-[[1-[(3-chlorothien-2-yl)methyl]propyl]amino]-3H-imidazo[4,5-b]pyrid-3-yl] N-ethyl 2,3-dihydroxycyclopentanecarboxamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / potassium fluoride; 1-methyl-2-pyrrolidinone; 18-crown-6 / 2 h / 100 °C

2.1: potassium tert-butoxide / tetrahydrofuran / 0.25 h / 20 °C

2.2: 83 percent / tetrahydrofuran / 1 h / 65 °C

3.1: 100 percent / potassium carbonate; 1-methyl-2-pyrrolidinone / 1.5 h / 85 °C

4.1: 97 percent / H₂ / platinum on carbon / ethyl acetate; methanol / 24 h / 20 °C / 2585.81 - 2844.39 Torr

5.1: 75 percent / Ac₂O / 2 h / 100 - 105 °C

6.1: Mg; I₂ / methanol; toluene / 3 h / 40 °C

7.1: conc. HCl / tetrahydrofuran / 3 h / 20 °C

7.2: 75 percent / aq. Na₂CO₃ / various solvent(s) / 16 h / 20 °C

With 1-methyl-pyrrolidin-2-one; hydrogenchloride; potassium fluoride; 18-crown-6 ether; potassium tert-butylate; hydrogen; iodine; acetic anhydride; potassium carbonate; magnesium; platinum on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; toluene; 1.1: Substitution / 2.1: deprotonation / 2.2: Substitution / 3.1: Substitution / 4.1: Hydrogenolysis / 5.1: cyclocondensation / 6.1: Reduction / 7.1: acetonide cleavage / 7.2: deprotonation;
DOI:10.1021/jo001066f