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

HRID 751059

Reaction equation

HRID 751059 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[O:10][C:6]=2[C:5]([C:12]#[N:13])=[CH:4][CH:3]=1.N(C1C2CCCCC=2C(C#N)=CC=1)=C=O.[OH:29][C@H:30]1[C@@H:37]2[N:33]([C:34](=[O:51])N(C3C4CCCCC=4C(C#N)=CC=3)[C:36]2=[O:38])[CH2:32][CH2:31]1>>[OH:29][C@H:30]1[C@@H:37]2[N:33]([C:34](=[O:51])[N:1]([C:2]3[C:7]4[N:8]=[C:9]([CH3:11])[O:10][C:6]=4[C:5]([C:12]#[N:13])=[CH:4][CH:3]=3)[C:36]2=[O:38])[CH2:32][CH2:31]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 218749104-Amino-7-cyano-2-methylbenzoxazoleHCID 597543044-Isocyanato-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Product 1

HCID 59754247(7R,7aS)-4-(7-Hydroxy-1,3-dioxotetrahydro-pyrrolo[1,2-c]imidazol-2-yl)-2-methylbenzoxazole-7-carbonitrile

Procedure

The title compound was prepared from 11C by procedures analogous to those described in Example 2 (2E to 2F) to give the product as a white foam. HPLC: 99% pure at 10.55 min (retention time) (CHIRALPAK® OD column 4.6×250 mm; 25% isopropanol in hexane over 30 min, 1 mL/min, monitoring at 220 nm); MS (ES) m/z 313 [M+1]+.

Sources & evidence

ORD record
ord-0d6104dcf20e47609c24d4b66e457dc0
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Linked notes

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