2,6-Lutidine → N'-[5-(6-Chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazol-3-yl]-N,N-dimethyl-formamidine

HRID 2053440Notes

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(Cl)(=O)=O.[N:30]1[C:35](C)=CC=C[C:31]=1C>CN(C=O)C>[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]([N:1]=[CH:31][N:30]([CH3:35])[CH3:25])[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)(15 mg, 0.045 mmol), methanesulfonyl chloride (7.4 mg, 0.065 mmol), 2,6-lutidine (7.4 mg, 0.068 mmol), and DMF (0.1 mL) was stirred at 25° C. for 2 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 20 mins to give 15 mg (68%) the title cpd as a TFA salt. 1H NMR (400 MHz, DMSO-d6) δ 12.62 (s, 1H), 8.52 (s, 1H), 7.68 (dd, 1H), 7.48 (m, 4H), 7.32 (m, 2H), 6.96 (d, 1H), 6.80 (s, 1H), 3.25 (s, 3H), 3.12 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C21H17ClN4O2 392.1, found 393.1 (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 20 mins

Sources & evidence

ORD record: ord-4ddc28f13c6d4107b460b635ad897642
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326788B2

Reaction notes

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