Benzaldehyde → HCID 12003998, compound

HRID 2245873Notes

Reaction equation

HRID 2245873 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](=O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=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]([CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=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

3

Reactant 2

HCID 240BenzaldehydeHCID 58815981HCID 58815981, compound

Product 1

HCID 12003998HCID 12003998, compoundYield 34.4%

Procedure

The title compound was made by a procedure identical to that of Example 66 with 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 0.64 g of benzaldehyde (6.07 mmol) to give 0.61 g (34%) of the desired compound as a light yellow solid. 1H NMR (300 MHz, d6-DMSO): □ 1.00-1.02 (d, J=4.7 Hz, 6H); 1.15-1.19 (t, 3H), 1.87-2.00 (m, 2H); 2.48-2.65 (m, 8H); 3.25 (s, 2H); 3.36-3.57 (m, 5H); 3.73-3.77 (dd, 1H); 4.03-4.10 (q, 2H); 4.96 (s, 1H); 6.62-6.69 (m, 3H); 7.08-7.42 (m, 10H); 9.35 (s, 1H). Calculated for C35H44N4O4.0.16 CH2Cl2: C, 70.58; H, 7.47; N, 9.36. Found: C, 70.57; H, 7.52; N, 9.39.

Sources & evidence

ORD record
ord-9e7b2d94baeb4dd49b065773a3bf5df7
Source dataset
uspto-grants-2010_03
Patent number
US07683168B2

Reaction notes

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