Water → HCID 23589568, compound

HRID 1295752Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of Example 53 (16 mg, 51 μmol) in pyridine (1 mL) at 0° C. was added 4-methyl-3-[(methylsulfonyl)aniline (4.4 μL, 87 μmol). The reaction mixture was stirred for 1 hr at 0° C. and then warmed to 25° C. and stirred for 4 hrs. Water (5 mL) was added and the mixture was extracted with ethyl acetate (3×5 mL). The combined organic extracts were washed with water (10 mL) and brine (10 mL) and dried (Na2SO4). The crude material was purified by chromatography on silica gel eluting with 2% methanol in chloroform to provide 6.9 mg (30%) of solid. MS: [M+H]+=390.2; 1H NMR (CDCl3): δ 7.93 (s, 1H), 7.86 (s, 1H), 7.77 (s, 1H), 7.35 (d, J=8.2 Hz, 1H), 7.27 (s, 1H), 7.18 (d, J=8.2 Hz, 1H), 6.25 (s, 1H), 3.82 (s, 3H), 3.03 (s, 3H), 2.86 (s, 3H), 2.24 (s, 3H)

Workup

temperaturewarmed to 25° C.
stirringstirred for 4 hrs
extractionthe mixture was extracted with ethyl acetate (3×5 mL)
washThe combined organic extracts were washed with water (10 mL) and brine (10 mL)
dry with materialdried (Na2SO4)
customThe crude material was purified by chromatography on silica gel eluting with 2% methanol in chloroform

Sources & evidence

ORD record: ord-9c3d2ef5f7a140dab82c127f5bedb37c
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244733B2

Reaction notes

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