Cyclopropanecarboxaldehyde → HCID 58815958, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:35])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C@@H:19]([N:27]3[CH2:32][C@@H:31]([CH3:33])[NH:30][CH2:29][C@@H:28]3[CH3:34])[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=3)[CH:14]=2)[CH2:8][CH2:7]1)[CH3:2].[CH:37]1([CH:40]=O)[CH2:39][CH2:38]1>>[CH2:1]([O:3][C:4](=[O:36])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:35])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C@@H:19]([N:27]3[CH2:32][C@@H:31]([CH3:33])[N:30]([CH2:40][CH:37]4[CH2:39][CH2:38]4)[CH2:29][C@@H:28]3[CH3:34])[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=3)[CH:14]=2)[CH2:8][CH2:7]1)[CH3:2]Participants
Procedure
The title compound was made by a procedure identical to that of Example 66 except that a shorter reaction time (2 hours) was used to combine 1.50 g of (4-{3-[(R)-((2S,5R)-2,5-dimethyl-piperazin-1-yl)-(3-hydroxy-phenyl)-methyl]-benzoyl}-piperazin-1-yl)-acetic acid ethyl ester (3.03 mmol) and 0.43 g of cyclopropanecarboxaldehyde (6.07 mmol, 2 equiv.) to give 0.73 g (44%) of the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO): □ 0.02-0.03 (t, 2H); 0.38-0.41 (d, J=7.7 Hz, 2H); 0.73-0.75 (m, 1H); 0.85-0.87 (d, J=5.8 Hz, 3H); 1.07-1.09 (d, J=6.0 Hz, 3H); 1.14-1.19 (t, 3H), 1.76-1.79 (m, 1H); 2.07-2.20 (ddd, 2H); 2.30-2.36 (dd, 1H); 2.48-2.51 (m, 6H); 2.86-2.89 (dd, 1H); 3.24 (s, 2H); 3.37-3.59 (m, 5H); 4.02-4.09 (q, 2H); 5.03 (s, 1H); 6.62-6.66 (m, 3H); 7.09-7.20 (m, 2H); 7.32-7.37 (m, 3H); 9.35 (s, 1H). Calculated for C32H44N4O4.0.20 CH2Cl2: C, 68.37; H, 7.91; N, 9.90. Found: C, 68.38; H, 7.97; N, 9.91.
Workup
- customexcept that a shorter reaction time (2 hours)
Sources & evidence
- ORD record
- ord-d7e1a9260ea44b3fa972dc4b73c58f4c
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683168B2
Reaction notes
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