(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)-2,3-dihydrobenzofuran-7-carbonitrile

HRID 501517Notes

Reaction equation

HRID 501517 reaction equation
[C:1]([C:3]1[C:11]2[O:10][CH2:9][CH2:8][C:7]=2[C:6]([NH:12][C:13](=[O:15])[CH3:14])=[CH:5][CH:4]=1)#[N:2].Cl.NC1C2CCCCC=2C(C#N)=CC=1.[OH:30][C@H:31]1[C@@H]2[N:34]([C:35](=[O:52])N(C3C4CCCCC=4C(C#N)=CC=3)C2=O)[CH2:33][CH2:32]1>>[OH:30][C@H:31]1[C@@H:14]2[N:34]([C:35](=[O:52])[N:12]([C:6]3[C:7]4[CH2:8][CH2:9][O:10][C:11]=4[C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[C:13]2=[O:15])[CH2:33][CH2:32]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 68459223N-(7-Cyano-2,3-dihydrobenzofuran-4-yl)-acetamideHCID 1317269774-Amino-5,6,7,8-tetrahydronaphthalene-1-carbonitrile, hydrochloride salt

Product 1

HCID 59754222(7R,7aS)-4-(7-Hydroxy-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)-2,3-dihydrobenzofuran-7-carbonitrile

Procedure

The title compound as a white solid was prepared from compound 4B by procedures analogous to those described in Example 2 (from 2D to 2F). HPLC: 100% at 3.43 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=13.69 min (100%); Conditions: OD (4.6×250 mm); Eluted with 25% isopropanol in hexane for 30 min at 1 mL/min. MS (ES) m/z 300 [M+1]+.

Workup

  1. washEluted 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)
  2. washEluted with 25% isopropanol in hexane for 30 min at 1 mL/min

Sources & evidence

ORD record
ord-8627482d5cee4e438b2966e663b3c158
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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