Isopropyl isocyanate → HCID 68432585, compound
Reaction equation
[CH2:1]([N:8]([CH3:26])[CH2:9][CH2:10][CH:11]1[CH2:16][N:15]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:14](=[O:25])[CH2:13][NH:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:27]([N:30]=[C:31]=[O:32])([CH3:29])[CH3:28]>>[CH2:1]([N:8]([CH3:26])[CH2:9][CH2:10][CH:11]1[CH2:16][N:15]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[C:14](=[O:25])[CH2:13][N:12]1[C:31]([NH:30][CH:27]([CH3:29])[CH3:28])=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
The title compound was prepared from 5-{2-[benzyl(methyl)amino]-ethyl}-1-(4-fluorobenzyl)piperazine-2-one (1.15 g, 3.23 mmol) and isopropyl isocyanate (0.412 g, 4.84 mmol) essentially according to the procedure described in Example 6, Step 8. The crude product was purified by silica gel chromatography (120 g RediSep column, 85 mL/min, gradient elution with EtOAc for 4 min, then with 0-10% MeOH-EtOAc over 15 min, then with 10% MeOH-EtOAc for 11 min) to afford the title compound as a viscous, light orange oil. 1H NMR (400 MHz, CDCl3): δ 7.34-7.19 (br m, 7 H), 7.03-6.98 (m, 2 H), 5.59 (m, 1 H), 4.75 (d, J=11.6 Hz, 1 H), 4.58 (d, J=14.8 Hz, 1 H), 4.28 (d, J=11.6 Hz, 1 H), 4.18 (m, 1 H), 4.12 (d, J=6.0 Hz, 1 H), 3.93-3.87 (m, 1 H), 3.70 (d, J=14.8 Hz, 1 H), 3.54 (d, J=10.4 Hz, 1 H), 3.49-3.46 (br m, 1 H), 3.24 (d, J=10.4 Hz, 1 H), 2.83 (dd, J=1.2, 10.0 Hz, 1 H), 2.34-2.29 (m, 1 H), 2.18-2.14 (m, 4 H), 1.71-1.65 (m, 1 H), 1.47-1.42 (m, 1 H), 1.08 and 1.05 (d, J=5.2 Hz, rotamers, 6 H). ES MS (M+1)=441.6.
Workup
- customThe crude product was purified by silica gel chromatography (
- wash120 g RediSep column, 85 mL/min, gradient elution with EtOAc for 4 min
Sources & evidence
- ORD record
- ord-20a2caa2ba924952bc80807f1cb145b3
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820680B2
Reaction notes
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