Phosphorus pentachloride → HCID 67436031, compound

HRID 1663496Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[C:6]([NH:8][C:9]1[C:13]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]#[N:27])[CH:20]=3)[C:17](=[O:28])[O:16][N:15]=2)=[N:12][O:11][N:10]=1)=O)#[N:2].P(Cl)(Cl)(Cl)(Cl)Cl.C([BH3-])#N.[Na+]>C1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[CH2:6][NH:8][C:9]1[C:13]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([CH:20]=3)[C:26]#[N:27])[C:17](=[O:28])[O:16][N:15]=2)=[N:12][O:11][N:10]=1)#[N:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 3-cyano-N-{4-[4-(3-cyano-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}benzamide (30 mg, 72 μmol) in benzene (2 mL) at 0° C. was treated with phosphorus pentachloride (45 mg, 0.22 mmol) and stirred at 90° C. for 2 h. The reaction mixture was concentrated, diluted with ethanol (2.5 mL), treated with sodium cyanoborohydride (14 mg, 0.22 mmol), and stirred for 16 h. The reaction mixture was purified by preparative LCMS to give the intermediate 5-[3-{4-[(3-cyanobenzyl)amino]-1,2,5-oxadiazol-3-yl}-5-oxo-1,2,4-oxadiazol-4(5H)-yl]-2-fluorobenzonitrile. This material was diluted with ethanol (1 mL), treated with 2.0 M sodium hydroxide in water (0.2 mL), and stirred for 45 min. Purification of the crude reaction mixture by preparative HPLC gave the desired product (3 mg, 11%). LCMS for C18H13FN7O2 (M+H)+: m/z=378.0.

Workup

concentrationThe reaction mixture was concentrated
additiondiluted with ethanol (2.5 mL)
stirringstirred for 16 h
customThe reaction mixture was purified by preparative LCMS

Sources & evidence

ORD record: ord-8b1b33b5aee349c28c156bc29ef0c639
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034953B2

Reaction notes

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