Cyclohexene → HCID 67187623, compound

HRID 885992Notes

Reaction equation

[CH3:1][C:2]1([CH3:33])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([NH:22][C:23]5[CH:28]=[CH:27][CH:26]=[C:25](/[CH:29]=[CH:30]/[O:31][CH3:32])[N:24]=5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.C1CCCCC=1>CCO.[Pd]>[CH3:1][C:2]1([CH3:33])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[C:19]([NH:22][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][O:31][CH3:32])[N:24]=5)[CH:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of Example 441 (100 mg, 0.2 mmol) in EtOH (4 mL) was added cyclohexene (1 mL) and palladium on carbon (120 mg, 10% wt). The reaction mixture was heated at 120° C. under microwave irradiation for 1 h. Additional palladium on carbon (40 mg, 10% wt) was added and the reaction mixture heated at 130° C. under microwave irradiation for 5 h. The reaction mixture was filtered through celite and concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (12.5 mg, 12.5%) as a brown solid. δH (CDCl3) 8.11 (1H, d, J 2.4 Hz), 7.42 (1H, dd, J 8.1 and 7.3 Hz), 7.01 (1H, dd, J 8.9 and 2.4 Hz), 6.92 (1H, d, J 8.7 Hz), 6.68 (1H, d, J 7.9 Hz), 6.64 (1H, d, J 7.3 Hz), 6.42 (1H, br. s), 5.15 (1H, br. s), 4.26-4.38 (2H, m), 4.18-4.08 (2H, m), 3.76 (2H, t, J 6.8 Hz), 3.36 (3H, s), 2.94 (2H, t, J 6.8 Hz), 2.87 (2H, s), 1.39 (6H, s). LCMS (ES+) 466.18 (M+H)+, RT 2.17 minutes (Method 1).

Workup

temperaturethe reaction mixture heated at 130° C. under microwave irradiation for 5 h
filtrationThe reaction mixture was filtered through celite and
concentrationconcentrated in vacuo
customPurification by preparative HPLC (Method 6)

Sources & evidence

ORD record: ord-29bf043dc19e4225ae17ad1b9e3994e8
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242116B2

Reaction notes

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