1-[2-Chloro-1-hydroxy-3-(6-quinolinyl)propyl]-2,5-pyrrolidinedione → Methyl 2-chloro-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoate

HRID 1508275Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([Cl:18])[CH:9]=2)=[CH:6][N:7]=1.Cl[CH:20]([CH2:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]=[CH:36][CH:35]=[CH:34]2)[CH:21](N1C(=O)CCC1=O)O>C(O)CCC>[Cl:18][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[N:7][C:2]3[N:3]([C:20]([CH2:30][C:31]4[CH:32]=[C:33]5[C:38](=[CH:39][CH:40]=4)[N:37]=[CH:36][CH:35]=[CH:34]5)=[CH:21][N:1]=3)[N:4]=2)[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: 110 °C

Procedure

The mixture of methyl 4-(3-amino-1,2,4-triazin-6-yl)-2-chlorobenzoate (Step 2, 0.840 g, 3.17 mmol) and 1-(2-chloro-1-hydroxy-3-quinolin-6-ylpropyl)pyrrolidine-2,5-dione (1.11 g, 3.49 mmol, Example 1, Step 7) in 1-butanol (11.6 mL) was stirred at 110° C. for 22 h. The solvent was removed under reduced pressure. The residue was triturated with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate and hexane to yield the desired product (0.908 g). The mother liquor was concentrated to half volume. The precipitate was collected by filtration and washed with ethyl acetate and hexane to afford additional desired product (0.342 g). The total product obtained was 1.10 g (80.6%). LCMS (M+H)+: m/z=430.0/431.9.

Workup

customThe solvent was removed under reduced pressure
customThe residue was triturated with ethyl acetate
filtrationThe precipitate was collected by filtration
washwashed with ethyl acetate and hexane

Sources & evidence

ORD record: ord-9f1bfa5698f7490da363083be6eff65e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221824B2

Reaction notes

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