7-Benzyl-5-(3-ethanesulfonyl-phenyl)-3-methyl-7,9-dihydro-dipyrido[2,3-b; 4',3'-d]pyrrol-8-one → 5-(3-Ethanesulfonyl-phenyl)-3-methyl-7,9-dihydro-dipyrido[2,3-b; 4',3'-d]pyrrol-8-one
Reaction equation
C([N:8]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])[CH:23]=2)[C:11]2[C:12]3[CH:18]=[C:17]([CH3:19])[CH:16]=[N:15][C:13]=3[NH:14][C:10]=2[C:9]1=[O:33])C1C=CC=CC=1>C(OC(=O)C)(=O)C>[CH2:31]([S:28]([C:24]1[CH:23]=[C:22]([C:20]2[C:11]3[C:12]4[CH:18]=[C:17]([CH3:19])[CH:16]=[N:15][C:13]=4[NH:14][C:10]=3[C:9](=[O:33])[NH:8][CH:21]=2)[CH:27]=[CH:26][CH:25]=1)(=[O:29])=[O:30])[CH3:32]Participants
3
Procedure
Compound 30 (24 mg, 0.053 mmol) was stirred in acetic anhydride (2 mL) at reflux overnight. Solvent was removed in vacuo, and the residue was subjected to hydrogenation with 20% palladium hydroxide on carbon (25 mg) in acetic acid (5 mL) under a balloon of hydrogen at 36° C. for 4 h. The reaction was filtered through Celite and concentrated in vacuo. Purification by prep HPLC gave 4.6 mg (24%) of the title compound as a white solid. 1H NMR (400 MHz, MeOD-d4/CDCl3): δ 8.41 (br s, 1H), 8.12 (s, 1H), 8.02 (d, 1H, J=8.0 Hz), 7.92 (d, 1H, J=8.0 Hz), 7.80 (t, 1H, J=8.0 Hz), 7.67 (s, 1H), 7.30 (br s, 1H), 7.14 (s, 1H), 3.25 (q, 2H, J=7.2 Hz), 2.35 (s, 3H), 1.31 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C19H17N3O3S, 368; found 368.
Workup
- temperatureat reflux overnight
- customSolvent was removed in vacuo
- filtrationThe reaction was filtered through Celite
- concentrationconcentrated in vacuo
- customPurification by prep HPLC
Sources & evidence
- ORD record
- ord-0367f64eade648baa3d1f02d3e26b093
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318939B2
Reaction notes
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