Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178455879, compound

HRID 1857043Notes

Reaction equation

HRID 1857043 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.C(NC(C1CCC(O)C1O)=O)C.Cl[C:28]1[CH:33]=[CH:32][NH:31][C:30](=[O:34])[C:29]=1[N+:35]([O-:37])=[O:36].[Cl:38][C:39]1[CH:43]=[CH:42][S:41][C:40]=1[CH2:44][C@@H:45]([CH2:47][CH3:48])[NH2:46]>>[Cl:38][C:39]1[CH:43]=[CH:42][S:41][C:40]=1[CH2:44][C@H:45]([NH:46][C:28]1[CH:33]=[CH:32][N:31]=[C:30]([OH:34])[C:29]=1[N+:35]([O-:37])=[O:36])[CH2:47][CH3:48]

Participants

5

Reactant 4

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 5192824-Chloro-3-nitro-1,2-dihydropyridin-2-oneHCID 11041539(R)-3-chloro-alpha-ethyl-2-thiopheneethanamineHCID 23103472N-ethyl-2,3-dihydroxycyclopentanecarboxamide

Product 1

HCID 178455879HCID 178455879, compound

Procedure

A method for preparing the dihydrochloride salt of [1S-[1a,2b,3b,4a(S*)]]-4-[7-[[1-(3-chloro-2-thienyl) methyl]propyl]amino]-3H-imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentanecarboxamide comprising the steps of reacting 4-chloro-3-nitropyridin-2(1H)-one with (R)-3-chloro-α-ethyl-2-thiopheneethanamine to form (R)-N-[1-[(3-chloro-2-thienyl)methyl]propyl]-2-hydroxy-3-nitro-4-pyridinamine, followed by replacing the hydroxy moiety of (R)-N-[1-[(3-chloro-2-thienyl)methyl]propyl]-2-hydroxy-3-nitro-4-pyridinamine with a chloro group to form (R)-2-chloro-N-[1-[(3-chloro-2-thienyl)methyl]propyl]-3-nitro-4-pyridinamine, followed by reacting (R)-2-chloro-N-[1-[(3-chloro-2-thienyl)methyl]propyl]-3-nitro-4-pyridinamine wit 2R,3S-isopropylidenedioxy-4R-amino-1S-ethylaminocarbonylcyclopentane to form [3aR-[3aa,4a,6a(R*),6aa]]-6-[[4-[[1-[(3-chloro-2-thienyl)methyl]propyl]amino]-3-nitro-2-pyridinyl]amino, followed by reducing [3aR-[3aa,4a,6a(R*),6aa]]-6-[[4-[[1-[(1-chloro-2-thienyl)methyl]propyl]amino]-3-nitro-2-pyridinyl]amino to [3aR-[3aa,4a,6a(R*),6aa]]-6-[[3-amino-4-[[1-[(3-chloro-2-thienyl)methyl]propyl]amino]-2-pyridinyl]amino]-N-ethyltetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide, followed by hydrolyzing [3aR-[3aa,4a,6a(R*),6aa]]-6-[[3-amino-4-[[1-[(3-chloro-2-thienyl)methyl]propyl]amino]-2-pyridinyl]amino]-N-ethyltetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide, in the presence of hydrochloric acid, said steps being effected in a concatenated manner, without a necessity for interim isolation and purification of intermediate compounds [3aR-[3aa,4a,6a(R*),6aa]]-6-[[3-amino-4-[[1-[(3-chloro-2-thienyl)methyl]propyl]amino]-2-pyridinyl]amino]-N-ethyltetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide, [3aR-[3aa,4a,6a(R*)6aa]]-6-[[4-[[1-[(3-chloro-2-thienyl)methyl]propyl]amino]-3-nitro-2-pyridinyl]amino]-N-ethyltetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide,(R)-2-chloro-N-[1-[(3-chloro-2-thienyl) methyl]propyl]-3-nitro-4-pyridinamine or (R)-N-[1-[(3-chloro-2-thienyl)methyl]propyl]-2-hydroxy-3-nitro-4-pyridinamine.

Sources & evidence

ORD record
ord-18b47690d1ad42748289c39be72c1cb4
Source dataset
uspto-grants-2000_11
Patent number
US06143894

Reaction notes

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