Hydroxyamine hydrochloride → HCID 44199933, compound

HRID 2061162Notes

Reaction equation

Cl.[NH2:2]O.[C:4](/[N:12]=[C:13](\SC)/[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([C:22]2[C:23](=[O:34])[N:24]([CH3:33])[C:25]3[C:30]([CH:31]=2)=[CH:29][N:28]=[C:27]([CH3:32])[CH:26]=3)[CH:16]=1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CCO>[CH3:33][N:24]1[C:25]2[C:30](=[CH:29][N:28]=[C:27]([CH3:32])[CH:26]=2)[CH:31]=[C:22]([C:17]2[CH:16]=[C:15]([NH:14][C:13]3[N:12]=[C:4]([C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)[O:11][N:2]=3)[CH:20]=[CH:19][C:18]=2[CH3:21])[C:23]1=[O:34]

Participants

Conditions

Temperature: 80 °C

Procedure

Hydroxylamine hydrochloride (35 mg, 0.5 mmol) and EtOH (1 mL) were added to the crude 21 (0.05 mmol). The mixture was heated at 80° C. for 2 h. After filtration, the mixture was purified by preparative LC/MS to give 1,7-dimethyl-3-(2-methyl-5-(5-phenyl-1,2,4-oxadiazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one A7. 1H NMR (400 MHz, d4-MeOH) δ 9.03 (s, 1H), 8.12 (s, 1H), 8.1 (d, J=1.5 Hz, 1H), 8.05 (s, 1H), 7.83 (s, 1H), 7.65 (d, J=6.2 Hz, 1H), 7.59 (d, J=6.3 Hz, 1H), 7.57 (d, J=7.2 Hz, 1H), 7.5 (d, J=2.4 Hz, 1H), 7.43 (dd, J=8.3, 2.5 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 3.84 (s, 3H), 2.83 (s, 3H), 2.18 (s, 3H). MS m/z 424.1 (M+1).

Workup

filtrationAfter filtration
customthe mixture was purified by preparative LC/MS

Sources & evidence

ORD record: ord-ce5c2ce3099e42d6b0ed9c81bd55cb06
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278452B2

Reaction notes

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