Isobutylene oxide → HCID 59716841, compound

HRID 2224226Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[CH3:25][C:26]1([O:29][CH2:28]1)[CH3:27].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[N:15]([CH2:25][C:26]([OH:29])([CH3:28])[CH3:27])[N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (20 mg, 0.056 mmol), prepared as described in Example 1, in 0.6 mL of DMF was added isobutylene oxide (4.0 mg, 0.056 mmol), followed by K2CO3 (15.5 mg, 0.112 mmol). The mixture was heated to 85° C. After stirring overnight, the reaction was allowed to cool to RT The reaction mixture was filtered (to remove excess of K2CO3). The collected solution was concentrated under reduced pressure. The crude product was purified by reverse phase HPLC to give the title compound, 7,8-bis(4-chlorophenyl)-2-(2-hydroxy-2-methylpropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (18.4 mg, 77% yield) as a yellow oil. MS [M+H]+: found 429; 1H NMR (CDCl3, 400 MHz) δ 8.28 (s, 1H), 7.39-7.27 (m, 6H), 7.16-7.12 (m, 2H), 4.16 (s, 2H), 4.00 (s, 1H), 1.34 (s, 6H).

Workup

temperatureto cool to RT The reaction mixture
filtrationwas filtered
custom(to remove excess of K2CO3)
concentrationThe collected solution was concentrated under reduced pressure
customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-aba43ead3436432c8c4f28482b611dca
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378418B2

Reaction notes

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