(7R,7aS)-4-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile → (7R,7aS)-3-Chloro-5-(7-hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)pyridine-2-carbonitrile

HRID 751090Notes

Reaction equation

HRID 751090 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([Cl:10])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[OH:11][C@H:12]1[C@@H:19]2[N:15]([C:16](=[O:33])N(C3C4CCCCC=4C(C#N)=CC=3)[C:18]2=[O:20])[CH2:14][CH2:13]1>>[Cl:10][C:4]1[C:5]([C:8]#[N:9])=[N:6][CH:7]=[C:2]([N:1]2[C:18](=[O:20])[C@@H:19]3[C@H:12]([OH:11])[CH2:13][CH2:14][N:15]3[C:16]2=[O:33])[CH:3]=1

Participants

3

Reactant 2

HCID 9904811(7R,7aS)-4-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrileHCID 218750995-Amino-3-chloropyridine-2-carbonitrile

Product 1

HCID 59754319(7R,7aS)-3-Chloro-5-(7-hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)pyridine-2-carbonitrile

Procedure

The title compound was synthesized from compound 44D by procedures analogous to those described for Examples 2E to 2F. HPLC: 100% at 1.67 min. (retention time) (Conditions: Shim-Pak VP-ODS (4.6×50 mm); Eluted with 0% to 100% B, 4 min gradient, 1 min hold. (A=90% H2O—10% MeOH—0.1% H3PO4 and B=10% H2O—90% MeOH—0.1% H3PO4); Flow rate at 4 mL/min UV detection at 220 nm); MS(ES) m/z 293 [M+H]+.

Workup

  1. washEluted with 0% to 100% B, 4 min gradient, 1 min hold

Sources & evidence

ORD record
ord-6076136b122740baa8f7f4bd6715f004
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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