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 1508272Notes

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-34476d89cc574ded82c7bdd913a78afb
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221824B2

Reaction notes

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