Azobisisobutyronitrile → HCID 58550991, compound

HRID 1908062Notes

Reaction equation

[CH3:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[C:7]3[C:8]3([CH2:14][CH2:13][N:12]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:10]3)[O:9][C:4]=2[CH:3]=1.[Br:28]N1C(=O)CCC1=O.C(C(N=NC(C)(C)C#N)(C)C)#N>C(Cl)(Cl)(Cl)Cl>[Br:28][CH2:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[C:7]3[C:8]3([CH2:10][CH2:11][N:12]([C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])[CH2:13][CH2:14]3)[O:9][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

7′-Methyl-1-(2,2,2-trifluoroacetyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1′-carbonitrile (250 mg, 0.666 mmol), 1-bromopyrrolidine-2,5-dione (119 mg, 0.666 mmol) and 2-(1-cyano-1-methyl-ethyl)azo-2-methyl-propanenitrile (10.9 mg, 0.0666 mmol) were combined in carbon tetrachloride and the mixture was heated at 80° C. for 4 hours. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography to give 7′-(bromomethyl)-1-(2,2,2-trifluoroacetyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1′-carbonitrile (53.2 mg, 18%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-20cbe830b55e4ce3b50b4af68061f427
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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