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

HRID 751100

Reaction equation

HRID 751100 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][C:4]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[N:2].N(C1C2CCCCC=2C(C#N)=CC=1)=C=O.[OH:31][C@H:32]1[C@@H:39]2[N:35]([C:36](=[O:53])N(C3C4CCCCC=4C(C#N)=CC=3)[C:38]2=[O:40])[CH2:34][CH2:33]1>>[OH:31][C@H:32]1[C@@H:39]2[N:35]([C:36](=[O:53])[N:7]([C:6]3[CH:5]=[C:4]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:3]([C:1]#[N:2])=[CH:9][CH:8]=3)[C:38]2=[O:40])[CH2:34][CH2:33]1

Participants

4

Reactant 3

HCID 9904811(7R,7aS)-4-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-5,6,7,8-tetrahydronaphthalene-1-carbonitrileHCID 441582825-Aminobiphenyl-2-carbonitrileHCID 597543044-Isocyanato-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Product 1

HCID 44425756(7R,7aS)-5-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)biphenyl-2-carbonitrile

Procedure

The title compound was prepared from compound 47A by procedures analogous to those described in Experiment 2E and 2F. HPLC: 96% at 3.24 min (retention time) (Conditions: YMC S5 C18 (4.6×50 mm); Eluted with 0% to 100% B, 8 min gradient, 3 min hold. (A=90% H2O—10% MeOH—0.1% H3PO4 and B=10% H2O—90% MeOH—0.1% H3PO4); Flow rate at 2.5 mL/min UV detection at 220 nm). LC/MS m/z 334 [M+H]+.

Workup

  1. washEluted with 0% to 100% B, 8 min gradient, 3 min hold

Sources & evidence

ORD record
ord-cf6f2373ddbd4c52b278cca04afdb61e
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Linked notes

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