Methanesulfonyl chloride → N-[5-(6-Chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazol-3-yl]-methanesulfonamide

HRID 2053441Notes

Reaction equation

[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:24])[NH:9][C:10]3[C:15]([C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:13]([Cl:23])=[CH:12][CH:11]=3)[O:4][N:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1>[Cl:23][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:24])[C:7]([C:5]1[O:4][N:3]=[C:2]([NH:1][S:26]([CH3:25])(=[O:28])=[O:27])[CH:6]=1)=[C:16]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A flask charged with 3-(3-amino-isoxazol-5-yl)-6-chloro-4-phenyl-1H-quinolin-2-one (Example 59)(17 mg, 0.050 mmol), methanesulfonyl chloride (7.5 mg, 0.066 mmol), and pyridine (0.2 mL) was stirred at 25° C. for 3 hrs. The reaction was concentrated and the title compound was purified by RP-HPLC, eluting with 40-70% CH3CN in 0.1% TFA/H2O over 10 mins to give 10 mg (50%). 1H NMR (400 MHz, CD3OD) δ 7.52 (dd, 1H), 7.46 (m, 3H), 7.36 (d, 1H), 7.22 (m, 2H), 7.12 (d, 1H), 6.54 (s, 1H), 3.00 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C19H14ClN3O4S 415.0, found 416.0 (M+H).

Workup

concentrationThe reaction was concentrated
customthe title compound was purified by RP-HPLC
washeluting with 40-70% CH3CN in 0.1% TFA/H2O over 10 mins
customto give 10 mg (50%)

Sources & evidence

ORD record: ord-a254577f288944bd9d8be381df33895b
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326788B2

Reaction notes

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