Diethyl Ether → HCID 9938761, compound
Reaction equation
[C:1]1([S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13]1([O:18][C:19]2[CH:20]=[C:21]([C@@H:27]([C:35]3[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=3)[CH2:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[CH:22]=[CH:23][C:24]=2[O:25][CH3:26])[CH2:17][CH2:16][CH2:15][CH2:14]1.CCOCC.[Cl:47]CCl>>[ClH:47].[CH:13]1([O:18][C:19]2[CH:20]=[C:21]([C@@H:27]([C:35]3[CH:36]=[CH:37][C:38]([NH:39][C:11]([NH:10][S:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)(=[O:8])=[O:9])=[O:12])=[CH:40][CH:41]=3)[CH2:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[CH:22]=[CH:23][C:24]=2[O:25][CH3:26])[CH2:17][CH2:16][CH2:15][CH2:14]1Participants
Procedure
Benzenesulphonylisocyanate (205 μl) was added dropwise to a solution of 4-[1-(R)-(3-cyclopentyloxy-4-methoxyphenyl)-2-(4-pyridyl)ethyl]aniline (500 mg prepared as described in International Patent specification No. WO95/17386) in dichloromethane (10 ml) under nitrogen at room temperature. The mixture was stirred or 30 min at this temperature and the solvent then removed in vacuo to yield a yellow gum. Trituration with ether furnished a pale yellow solid (the free base of the title compound which was disolved in dichloromethane (5 ml) and treated with ethereal HCl to afford a yellow solid. Subsequent recrystallisation of the solid from methanol yielded the title compound (450 mg) as an off white solid δH (CD3OD) 1.40-1.90 (8H, br m), 3.64 (2H, d, J 9 Hz), 3.72 (3H, s), 4.34 (1H, t, J 9 Hz), 4.72 (1H, m), 6.75 (3H, d+d+s), 7.20 (4H, d+d), 7.50-7.75 (3H, m), 7.72 (2H, d, J 8 Hz), 8.00 (2H, d, J 8 Hz), and 8.55 (2H, d, J 8 Hz).
Workup
- customthe solvent then removed in vacuo
- customto yield a yellow gum
Sources & evidence
- ORD record
- ord-e68161e8274a404bbdd8f4b89fceb4a4
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849770
Reaction notes
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