Azobisisobutyronitrile → HCID 69064593, compound

HRID 1817340Notes

Reaction equation

F[C:2](F)(F)[C:3]([O-:5])=O.C(O[C:11]([C:13]1[NH+:22]=[CH:21][C:20]([OH:23])=[C:19]2[C:14]=1[CH2:15][CH2:16][N:17]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:18]2=[O:24])=O)C.Br[N:34]1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[CH2:13]([N:22]1[CH2:21][C:20]([OH:23])=[C:19]2[C:14]([CH:15]=[CH:16][N:17]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[C:18]2=[O:24])=[C:2]1[C:3]([NH2:34])=[O:5])[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To solution of 5-(ethoxycarbonyl)-2-(4-fluorobenzyl)-8-hydroxy-1-oxo-1,2,3,4-tetrahydro-2,6-naphthyridin-6-ium trifluoroacetate (0.020 g, 0.045 mmol; see Example 8, Step 4) in CCl4 (2 mL) is added N-bromo succinimide (0.017 g, 0.095 mmol) and AIBN (catalytic). The reaction is heated to 80° C. for 1 hour, then concentrated and chromatographed on reverse phase to give the product.

Workup

concentrationconcentrated
customchromatographed on reverse phase
customto give the product

Sources & evidence

ORD record: ord-b7c3728e288a4288a4be83d9deda9ddd
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598264B2

Reaction notes

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