Trifluoroacetic acid → HCID 25230871, compound

HRID 657592Notes

Reaction equation

[Cl:1][C:2]1[CH:32]=[C:31]([N:33]2[C:38](=[O:39])[NH:37][C:36](=[O:40])[C:35]([C:41]#[N:42])=[N:34]2)[CH:30]=[C:29]([Cl:43])[C:3]=1[O:4][C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[C:8](=[O:14])[N:7]([CH2:15][O:16][P:17](=[O:28])([O:23]C(C)(C)C)[O:18]C(C)(C)C)[N:6]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:32]=[C:31]([N:33]2[C:38](=[O:39])[NH:37][C:36](=[O:40])[C:35]([C:41]#[N:42])=[N:34]2)[CH:30]=[C:29]([Cl:43])[C:3]=1[O:4][C:5]1[CH:10]=[C:9]([CH:11]([CH3:12])[CH3:13])[C:8](=[O:14])[N:7]([CH2:15][O:16][P:17](=[O:18])([OH:28])[OH:23])[N:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of phosphoric acid di-tert-butyl ester 3-[2,6-dichloro-4-(6-cyano-3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-phenoxy]-5-isopropyl-6-oxo-6H-pyridazin-1-ylmethyl ester (44.0 mg, 0.067 mmol) in methylene chloride (1.0 mL, 0.067M) at 25° C. was treated with trifluoroacetic acid (0.2 mL). The reaction mixture was stirred at 25° C. for 20 min. At this time, the reaction mixture was concentrated in vacuo, azeotropically dried with benzene and concentrated from absolute ethanol followed by lyophilization from acetonitrile and water to afford phosphoric acid mono-{3-[2,6-dichloro-4-(6-cyano-3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-phenoxy]-5-isopropyl-6-oxo-6H-pyridazin-1-ylmethyl}ester (31.4 mg, 86%) an off-white solid. Present in the product was 0.95 moles of residual ammonium from the ammonium acetate used in the supercritical fluid purification of the precursor. ES+-HRMS m/e calcd for C18H15N6O8PCl2 (M+Na+) 566.9958, found 566.9962.

Workup

concentrationAt this time, the reaction mixture was concentrated in vacuo
dry with materialazeotropically dried with benzene
concentrationconcentrated from absolute ethanol

Sources & evidence

ORD record: ord-e01a65ad82484e87a3f166c7ec74623b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076334B2

Reaction notes

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