Cyclopropanecarboxaldehyde → HCID 58815907, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:40])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:39])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C@@H:23]([N:31]3[CH2:36][C@@H:35]([CH3:37])[NH:34][CH2:33][C@@H:32]3[CH3:38])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=3)[CH:18]=2)[CH2:12][CH2:11]1)[CH3:2].[CH:41]1([CH:44]=O)[CH2:43][CH2:42]1>>[CH2:1]([O:3][C:4](=[O:40])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:39])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C@@H:23]([N:31]3[CH2:36][C@@H:35]([CH3:37])[N:34]([CH2:44][CH:41]4[CH2:43][CH2:42]4)[CH2:33][C@@H:32]3[CH3:38])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=3)[CH:18]=2)[CH2:14][CH2:15]1)[CH3:2]Participants
Procedure
The title compound was made by a procedure identical to that of Example 96 with 1.50 g of 6-(4-{3-[(R)-((2S,5 R)-2,5-dimethyl-piperazin-1-yl)-(3-hydroxy-phenyl)-methyl]-benzoyl}-piperazin-1-yl)-hexanoic acid ethyl ester (2.72 mmol) and 0.38 g of cyclopropanecarboxaldehyde (5.5 mmol) to give 0.63 g of desired compound as a white solid. 1H NMR (300 MHz, d6-DMSO): □ 0.02-0.03 (m, 2H); 0.38-0.41 (d, J=7.7 Hz, 2H); 0.73-0.75 (m, 1H); 0.86-0.88 (d, J=5.7 Hz, 3H); 1.08-1.10 (d, J=6.0 Hz, 3H); 1.12-1.17 (t, 3H), 1.21-1.28 (m, 2H); 1.37-1.55 (m, 4H); 1.73-1.80 (m, 1H); 2.07-2.33 (m, 8H); 2.48-2.62 (m, 5H); 2.86-2.89 (dd, 1H); 3.27-3.33 (m, 4H); 3.53-3.56 (m, 1H); 3.98-4.05 (q, 2H); 5.04 (s, 1H); 6.62-6.66 (m, 3H); 7.10-7.15 (t, 1H); 7.18-7.20 (dd, 1H); 7.32-7.40 (m, 3H); 9.34 (s, 1H). MS: 604.9 (M+1, 70%), 437.1 (50%), 209.1 (75%), 167.1 (100%). Calculated for C36H52N4O4 0.08 CH2Cl2: C, 70.85; H, 8.60; N, 9.16. Found: C, 70.89; H, 8.65; N, 8.86.
Sources & evidence
- ORD record
- ord-b05e15c072204a04aaae6a1cb3318f24
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683168B2
Reaction notes
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