O-Methylhydroxylamine hydrochloride → HCID 77845421, compound

HRID 595605Notes

Reaction equation

[C:1]([C:4]1[O:5][C:6]2[CH:16]=[C:15]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])[C:14]([C:23]3[CH:24]=[CH:25][C:26]4[O:39][CH2:38][N:29]5[C:30]6[CH:31]=[CH:32][CH:33]=[C:34]([F:37])[C:35]=6[CH:36]=[C:28]5[C:27]=4[N:40]=3)=[CH:13][C:7]=2[C:8]=1[C:9]([NH:11][CH3:12])=[O:10])(=O)[CH3:2].Cl.[CH3:42][O:43][NH2:44]>C(O)C.N1C=CC=CC=1>[F:37][C:34]1[C:35]2[CH:36]=[C:28]3[C:27]4[N:40]=[C:23]([C:14]5[C:15]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:19])=[O:20])=[CH:16][C:6]6[O:5][C:4](/[C:1](=[N:44]/[O:43][CH3:42])/[CH3:2])=[C:8]([C:9]([NH:11][CH3:12])=[O:10])[C:7]=6[CH:13]=5)[CH:24]=[CH:25][C:26]=4[O:39][CH2:38][N:29]3[C:30]=2[CH:31]=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution compound 2-acetyl-5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (50 mg, 0.088 mmol) in ethanol (1.5 mL) was added O-methylhydroxylamine hydrochloride (25 mg, 0.26 mmol) and 2 drops pyridine. The resulting mixture was stirred at 70° C. for 2 hours. The solvent was removed under reduced pressure and the residue was purified by prep-HPLC to give the product of (E)-5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(1-(methoxyimino)ethyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (20 mg, yield: 40%). 1H-NMR (CDCl3, 400 MHz) δ 9.56 (s, 1H), 8.65 (s, 1H), 7.67 (s, 1H), 7.48 (dd, J=10 Hz, 2H), 7.18˜7.23 (m, 2H), 7.10 (d, J=8.0 Hz, 1H), 6.84 (t, J=8.0 Hz, 1H), 5.99 (s, 2H), 4.12 (s, 3H), 3.41 (s, 3H), 2.99 (d, J=4.8 Hz, 3H), 2.66 (s, 3H), 2.41 (s, 3H). MS (M+H)+: 592.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by prep-HPLC

Sources & evidence

ORD record: ord-292b9fb1642e4dafb72c9e751419e542
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242998B2

Reaction notes

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