Hydroxyammonium hydrochloride → HCID 178483759, compound

HRID 1840421Notes

Reaction equation

[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][NH:5][C:6]1[C:18]2[C:17](=O)[C:16]3[CH:15]=[N:14][CH:13]=[CH:12][C:11]=3[C:10]=2[C:9]2[CH:20]=[CH:21][C:22]([OH:24])=[CH:23][C:8]=2[N:7]=1.Cl.[OH:27][NH3+:28]>N1C=CC=CC=1.ClCCl.CO>[CH3:25][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]1[C:18]2[C:17](=[N:28][OH:27])[C:16]3[CH:15]=[N:14][CH:13]=[CH:12][C:11]=3[C:10]=2[C:9]2[CH:20]=[CH:21][C:22]([OH:24])=[CH:23][C:8]=2[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The compound of Example 41(18.0 mg) and hydroxylammonium hydrochloride (20.0 mg) (Tokyo Kasei Ltd.) were dissolved in pyridine (0.5 ml) (Wako Pure Chemical Industries Ltd.) and the solution was stirred at 80° C. for 10 hours. The reaction mixture was diluted with dichloromethane and filtered through a glass filter. The solid obtained was dissolved in methanol and passed through a Mega Bond Elut SCX (Varian). The column was washed with methanol and the product was eluted with ammonia water (25%, Wako Pure Chemical Industries Ltd.)—methanol=5:95. The solvent was evaporated to dryness. The desired product was obtained as an orange solid. ESI−MS: m/z 350 (MH+); 1H-NMR (MeOH-d4): δ2.45 (6H, s), 2.74 (2H, t, J=6.3 Hz), 3.63 (2H, t, J=6.3 Hz), 6.81 (1H, dd, J=6.6 Hz, 2.3 Hz), 6.93 (1H, d, J=2.3 Hz), 7.77 (1H, d, J=5.3 Hz), 7.83 (1H, d, J=9.2 Hz), 8.42 (1H, d, J=5.3 Hz), 9.16 (1H, s).

Workup

filtrationfiltered through a glass
filtrationfilter
customThe solid obtained
washThe column was washed with methanol
washthe product was eluted with ammonia water (25%, Wako Pure Chemical Industries Ltd.)—methanol=5:95
customThe solvent was evaporated to dryness

Sources & evidence

ORD record: ord-a10291efa9de404088363560c2c9a07d
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680326B2

Reaction notes

Loading…