Azobisisobutyronitrile → HCID 58550944, compound

HRID 2204143Notes

Reaction equation

[C:1]([C:3]1[N:11]2[C:6]([C:7]3([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[O:8][C:9]3[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:10]=32)=[CH:5][CH:4]=1)#[N:2].[Br:29]N1C(=O)CCC1=O.C(C(N=NC(C)(C)C#N)(C)C)#N>C(Cl)(Cl)(Cl)Cl>[Br:29][CH2:16][C:14]1[CH:13]=[CH:12][C:10]2[N:11]3[C:3]([C:1]#[N:2])=[CH:4][CH:5]=[C:6]3[C:7]3([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[O:8][C:9]=2[CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 1′-cyano-7′-methyl-spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (200 mg, 0.527 mmol), 1-bromopyrrolidine-2,5-dione (93.8 mg, 0.527 mmol), and 2-(1-cyano-1-methyl-ethyl)azo-2-methyl-propanenitrile (8.66 mg, 0.0527 mmol) were combined in carbon tetrachloride (10 mL) and the mixture was heated at 80° C. for 4 hours. The mixture was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (50-100% CH2Cl2/hexanes) to yield tert-butyl 7′-(bromomethyl)-1′-cyano-spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (115 mg, 47%). ESI-MS m/z calc. 457.1, found 458.5 (M+1)+; Retention time 2.43 minutes (3 min run).

Workup

washThe mixture was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (50-100% CH2Cl2/hexanes)

Sources & evidence

ORD record: ord-a5cff5cf25a24a38b6f84cab3c81368a
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365588B2

Reaction notes

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