Acetic Acid → HCID 22171075, compound

HRID 1823231Notes

Reaction equation

[C:1]1([CH3:36])[CH:6]=[CH:5][C:4]([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:19][CH:20]([C:29]3[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)[CH2:21][S:22]([C:24]3[NH:28][N:27]=[CH:26][N:25]=3)=[O:23])=[N:8]2)=[CH:3][CH:2]=1.OO.C(O)(=[O:41])C.CO>CN(C)C=O>[C:1]1([CH3:36])[CH:2]=[CH:3][C:4]([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:19][CH:20]([C:29]3[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)[CH2:21][S:22]([C:24]3[NH:28][N:27]=[CH:26][N:25]=3)(=[O:41])=[O:23])=[N:8]2)=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a flask was added 5-[3-(1,5-di-p-tolyl-1H-pyrazol-3-yl)-2-m-tolyl-propane-1-sulfinyl]-1H-[1,2,4]triazole (Example 136; 25 mg, 0.05 mmol), hydrogen peroxide (0.15 mL, 30% solution in water) and acetic acid (0.1 ml). The mixture was heated at 50° C. for 24 h and then cooled. Methanol (0.5 mL) and N,N-dimethylformamide (0.5 mL) were added to dissolve the resulting precipitate. This solution was then purified directly by reversed-phase chromatography yielding the title compound (24 mg, 95%). HPLC: Rt=2.97 (Method B). MS (ESI): mass calculated for C29H29N5O2S, 511.20; m/z found, 512.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 14.87 (br s, 1H), 8.72 (s, 1H), 7.18 (d, J=8.2 Hz, 2H), 7.13 (d, J=8.0 Hz, 2H), 7.08 (d, J=7.0 Hz, 1H), 7.07-7.04 (m, 3H), 7.01-6.99 (m, 3H), 6.95 (d, J=7.4 Hz, 1H), 6.15 (s, 1H), 3.91 (d, J=6.6 Hz, 2H), 3.52-3.49 (m, 1H), 3.08 (dd, J=14.7, 7.6 Hz, 1H), 2.91 (dd, J=14.5, 7.4 Hz, 1H), 2.31 (s, 3H), 2.27 (s, 3H), 2.23 (s, 3H).

Workup

temperaturecooled
dissolutionto dissolve the resulting precipitate
customThis solution was then purified directly by reversed-phase chromatography

Sources & evidence

ORD record: ord-a2312eaa69e442dd9202d3b6c665724d
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037931B2

Reaction notes

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