(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-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-2-methylbenzofuran-7-carbonitrile

HRID 501535Notes

Reaction equation

HRID 501535 reaction equation
C(C1C2[O:10]C(C)=CC=2C(NC(=O)C(C)(C)C)=CC=1)#N.Cl.NC1C2CCCCC=2C(C#N)=CC=1.[OH:34][C@H:35]1[C@@H:42]2[N:38]([C:39](=[O:56])[N:40]([C:44]3[C:53]4[CH2:52][CH2:51][CH2:50]C[C:48]=4[C:47]([C:54]#[N:55])=[CH:46][CH:45]=3)[C:41]2=[O:43])[CH2:37][CH2:36]1>>[OH:34][C@H:35]1[C@@H:42]2[N:38]([C:39](=[O:56])[N:40]([C:44]3[C:53]4[CH:52]=[C:51]([CH3:50])[O:10][C:48]=4[C:47]([C:54]#[N:55])=[CH:46][CH:45]=3)[C:41]2=[O:43])[CH2:37][CH2:36]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 59754271N-(7-Cyano-2-methyl-benzofuran-4-yl)-2,2-dimethylpropionamideHCID 1317269774-Amino-5,6,7,8-tetrahydronaphthalene-1-carbonitrile, hydrochloride salt

Product 1

HCID 59754352(7R,7aS)-4-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-2-methylbenzofuran-7-carbonitrile

Procedure

The title compound was prepared from compound 10E by procedures analogous to those described in Experiment 2 (2D to 2F). HPLC: 99% at 4.2 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (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). Chiral HPLC: retention time=10.99 min (99%); Conditions: OD (4.6×250 mm); Eluted with 25% isopropanol in hexane for 30 min at 1 mL/min. MS (ES) m/z 312 [M+1]+.

Workup

  1. washEluted with 0% to 100% B, 8 min gradient
  2. washEluted with 25% isopropanol in hexane for 30 min at 1 mL/min

Sources & evidence

ORD record
ord-fae9bdcc16f6477d96062576e223b6ce
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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