Chlorosuccinimide → (R)-3-{(1S,2S)-1-[5-(2-Chloro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-5-[4-(2-hydroxy-ethoxy)-phenyl]-imidazolidine-2,4-dione

HRID 561986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561986
IC1C=CC(C2NC([C@@H](N3C(=O)[C@@H](CCC(O)=O)NC3=O)C(C)C)=NC=2)=CC=1.[Cl:29][C:30]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:31]=1I.C(O[C:43](=[O:66])[NH:44][C@H:45]([C:54]1[NH:55][C:56](C2C=CC=CC=2F)=[CH:57][N:58]=1)[C@H:46]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH3:47])(C)(C)C.ClN1C(=O)CCC1=O.C([O:79][C:80]([NH:82][C@H:83]([C:87]1[CH:92]=[CH:91][C:90]([O:93][CH2:94][C:95](=[O:99])N(C)C)=[CH:89][CH:88]=1)C(O)=O)=O)(C)(C)C.N[C@H](C1C=CC(OCCO)=CC=1)C(N[C@H](C1NC(C2C=CC(I)=CC=2Cl)=CN=1)[C@H](C1C=CC=CC=1)C)=O>>[Cl:29][C:30]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:31]=1[C:57]1[NH:58][C:54]([C@@H:45]([N:44]2[C:43](=[O:66])[C@@H:83]([C:87]3[CH:88]=[CH:89][C:90]([O:93][CH2:94][CH2:95][OH:99])=[CH:91][CH:92]=3)[NH:82][C:80]2=[O:79])[C@H:46]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH3:47])=[N:55][CH:56]=1

Komponenten

7

Edukt 6

HCID 31398ChlorosuccinimideHCID 534065552-Chloro-1,4-diiodobenzeneHCID 577719783-((R)-1-{(S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-methyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-propionic acidHCID 66815126(R)-tert-butoxycarbonylamino-(4-dimethylcarbamoylmethoxy-phenyl)-acetic acidHCID 67001455(R)-2-amino-N-{(1S,2S)-1-[5-(2-chloro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2-[4-(2-hydroxy-ethoxy)-phenyl]-acetamideHCID 67001749{(1S,2S)-1-[5-(2-fluoro-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 57771970(R)-3-{(1S,2S)-1-[5-(2-Chloro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-5-[4-(2-hydroxy-ethoxy)-phenyl]-imidazolidine-2,4-dione

Versuchsvorschrift

Prepared by the same method as described in example 1 except that (i) in step 35-A 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step F was omitted; and (iii) cyclization of (R)-2-amino-N-{(1S,2S)-1-[5-(2-chloro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2-[4-(2-hydroxy-ethoxy)-phenyl]-acetamide in step 35-H was performed as described in example 34. HR-MS: calcd for C29H26ClIN4O4 [M+H+] 657.07600. Found 657.0757.

Aufarbeitung

  1. customPrepared by the same method

Quellen und Nachweise

ORD-Eintrag
ord-80072353e4114c57bfea47b5a35b07b8
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063085B2

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