3-Fluorobenzaldehyde → HCID 58815980, compound

HRID 2245875Notes

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].[F:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][CH:49]=1)[CH:45]=O>>[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]([CH2:45][C:44]4[CH:47]=[CH:48][CH:49]=[C:42]([F:41])[CH:43]=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

Reactant 2

HCID 680093-Fluorobenzaldehyde

HCID 58815990HCID 58815990, compound

Product 1

HCID 58815980HCID 58815980, compoundYield 54.1%

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,5R)-2,5-dimethyl-piperazin-1-yl)-(3-hydroxy-phenyl)-methyl]-benzoyl}-piperazin-1-yl)-hexanoic acid ethyl ester (2.72 mmol) and 0.68 g of 3-fluorobenzaldehyde (5.5 mmol) to give 0.97 g of desired compound as a light yellow solid. 1H NMR (300 MHz, d6-DMSO): □ 1.01-1.03 (d, J=5.8 Hz, 6H); 1.12-1.17 (t, 3H), 1.22-1.29 (m, 2H); 1.35-1.56 (m, 4H); 1.90-2.02 (m, 2H); 2.23-2.33 (m, 7H); 2.48-2.66 (m, 6H); 3.25-3.33 (m, 3H); 3.54-3.56 (m, 1H); 3.72-3.76 (dd, 1H); 3.98-4.05 (q, 2H); 4.95 (s, 1H); 6.62-6.71 (m, 3H); 6.97-7.43 (m, 9); 9.34 (s, 1H). MS: 659.0 (M+1, 80%), 437.2(85%), 221.2(100%), 209.1(70%). Calculated for C39H51FN4O4 0.11 CH2Cl2: C, 70.30; H, 7.73; N, 8.38; F, 2.84. Found: C, 70.32; H, 7.78; N, 8.41; F, 3.00.

Sources & evidence

ORD record: ord-51b49f5084694834bcd10ac785391769
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683168B2

Reaction notes

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