1-[2-Chloro-1-hydroxy-3-(6-quinolinyl)propyl]-2,5-pyrrolidinedione → 6-((2-(4-Bromo-3-fluorophenyl)imidazo[1,2-b][1,2,4]triazin-7-yl)methyl)quinoline

HRID 452030Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([NH2:14])=[N:10][CH:9]=2)=[CH:4][C:3]=1[F:15].Cl[CH:17]([CH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][CH:32]=[CH:31]2)[CH:18](N1C(=O)CCC1=O)O>C(O)(C)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:17]([CH2:27][C:28]4[CH:29]=[C:30]5[C:35](=[CH:36][CH:37]=4)[N:34]=[CH:33][CH:32]=[CH:31]5)=[CH:18][N:14]=3)[N:13]=2)=[CH:4][C:3]=1[F:15]

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 6-(4-bromo-3-fluorophenyl)-1,2,4-triazin-3-amine (Step 5, 200 mg, 0.743 mmol) and 1-(2-chloro-1-hydroxy-3-quinolin-6-ylpropyl)pyrrolidine-2,5-dione (Step 7, 284 mg, 0.892 mmol) in isopropyl alcohol (7.4 mL) and water (0.11 mL) in a sealed tube was heated at 105° C. for 5 d. After the reaction mixture was cooled to ambient temperature, the precipitate was collected by filtration, washed with isopropanyl alcohol, and dried in vacuum to give the desired product (180 mg, 55%) LCMS (M+H)+: m/z=433.9/436.0.

Workup

temperatureAfter the reaction mixture was cooled to ambient temperature
filtrationthe precipitate was collected by filtration
washwashed with isopropanyl alcohol
customdried in vacuum

Sources & evidence

ORD record: ord-af0ea96374ff411fb2ecccf4aeebad48
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487096B2

Reaction notes

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