RO-05-2921 → HCID 19063673, compound
Reaction equation
[C:1]1([C:7]2[C:8]3[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=3[NH:10][C:11](=[O:14])[CH2:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][C:21]([N:23]([CH:32]([CH3:34])[CH3:33])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)=[O:22]>>[CH:32]([N:23]([C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[C:21](=[O:22])[CH2:20][N:10]1[C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=2[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:13][CH2:12][C:11]1=[O:14])([CH3:33])[CH3:34]Participants
Procedure
By employing conditions similar to those described in Intermediate 11, 5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one (Bock et. al., J. Org. Chem. 1987, 52, 3232-3239. 3.00 g, 12.71 mmol) and 2-bromo-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (3.820 g, 13.35 mmol) are converted to the title compound, which is obtained as a wet white solid. The product is dissolved in anhydrous DCM, dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue is triturated with n-hexane, filtered and dried overnight under vacuum to provide the title compound as a white solid (5.380 g, 12.18 mmol). 1H NMR (300 MHz, d6-DMSO) δ=0.91-0.97 (m, 6H); 3.70 (d, J=10.4 Hz, 1H); 3.76 (s, 3H); 4.08 (s, 2H); 4.51 (d, J=10.6 Hz, 1H); 4.67-6.78 (m, 1H); 6.97-7.63 (m, 13H). MS (FAB): [M+H]+ =442.
Sources & evidence
- ORD record
- ord-f0a92f0397ed4f26b1c4450579633c3f
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05795887
Reaction notes
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