Diisopropylethylamine → 4-[3-(5-Isoquinolinyl)-1,2,4-oxadiazol-5-yl]-1-(2-methylpropyl)-2(1H)-pyridinone

HRID 2192525Notes

Reaction equation

[CH3:1][CH:2]([CH3:14])[CH2:3][N:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:12])=O)=[CH:6][C:5]1=[O:13].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.O[NH:49][C:50]([C:52]1[C:53]2[CH:54]=[CH:55][N:56]=[CH:57][C:58]=2[CH:59]=[CH:60][CH:61]=1)=[NH:51]>CN(C=O)C>[CH:57]1[C:58]2[C:53](=[C:52]([C:50]3[N:49]=[C:10]([C:7]4[CH:8]=[CH:9][N:4]([CH2:3][CH:2]([CH3:1])[CH3:14])[C:5](=[O:13])[CH:6]=4)[O:12][N:51]=3)[CH:61]=[CH:60][CH:59]=2)[CH:54]=[CH:55][N:56]=1

Participants

Conditions

Temperature: 120 °C

Procedure

1-(2-Methylpropyl)-2-oxo-1,2-dihydro-4-pyridinecarboxylic acid (D28; 57 mg, 0.294 mmol) was stirred in DMF (0.5 ml) with HATU (122 mg, 0.321 mmol) and DIPEA (0.14 ml, 0.802 mmol) at room temperature for 30 mins before adding a solution of N-hydroxy-5-isoquinolinecarboximidamide (D1, 50 mg, 0.267 mmol) in DMF (0.5 ml). The resulting mixture was heated to 120° C. for 40 mins in a Biotage Initiator microwave. The solvent was removed under vacuum, and the residue was purified by column chromatography on silica, eluting with 0-4% methanol in dichloromethane. The relevant fractions were combined and concentrated under vacuum to give the title compound as a pale yellow oil (5 mg).

Workup

customThe solvent was removed under vacuum
customthe residue was purified by column chromatography on silica
washeluting with 0-4% methanol in dichloromethane
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-036ee4b6bfdb4bfda99cffdcefef0faa
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329730B2

Reaction notes

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