Hydroxyamine hydrochloride → HCID 72757836, compound

HRID 1986052Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=S)[CH:18]=2)=[CH:15][CH:14]=[C:13]([O:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:12]=3)=[CH:5][CH:4]=1.Cl.[NH2:31][OH:32]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=[N:31][OH:32])[CH:18]=2)=[CH:15][CH:14]=[C:13]([O:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:12]=3)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2-(4-methoxy-phenyl)-7-(3-morpholin-4-yl-propoxy)-chromene-4-thione (222.0 mg, 0.38 mmol) in 4.0 mL of pyridine was added 80.0 mg (1.15 mmol) of hydroxylamine hydrochloride. The solution was stirred at 110° C. for 2 h. The solvent was removed under vacuum and the residue was treated with ice. The resulting slurry was filtered. The filter cake was washed with H2O purified by prep HPLC to afford 71.4 mg (35.5% yield) of desired product, I-26, as a yellow syrup (TFA salt). 1H NMR (500 MHz, DMSO-d6) δ 10.71 (s br, 1H), 9.99 (s, 1H), 7.88 (d, 2H), 7.79 (d, 1H), 7.08 (d, 2H), 7.02 (d, 1H), 6.99 (s, 1H), 6.88(dd, 1H), 4.16(t, 2H), 4.02(d, 2H), 3.84 (s, 3H), 3.67(t, 2H), 3.52(d, 2H), 3.31(t, 2H), 3.12(m, 2H), 2.17 (m, 2H) ppm. LC/MS: 411.2 (M+H), HPLC/Method A (Rt 4.03 min, 98.0% purity).

Workup

customThe solvent was removed under vacuum
additionthe residue was treated with ice
filtrationThe resulting slurry was filtered
washThe filter cake was washed with H2O
custompurified by prep HPLC

Sources & evidence

ORD record: ord-5759b4c2e5e64809aa0d0628c4599560
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547794B2

Reaction notes

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