2-(5-(diethylamino)-2-(3-(1-hydroxy-3,6,9,12-tetraoxapentadec-14-yn-15-yl)benzamido)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide → 2-(5-(diethylamino)-2-(3-(1-hydroxy-3,6,9,12-tetraoxapentadecan-15-yl)benzamido)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

HRID 625496Notes

Reaction equation

HRID 625496 reaction equation
[CH2:1]([N:3]([CH2:55][CH3:56])[C:4]1[CH:5]=[CH:6][C:7]([NH:30][C:31](=[O:54])[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]#[C:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][OH:53])[CH:33]=2)=[C:8]([C:10]2[CH:11]=[C:12]([CH:27]=[CH:28][N:29]=2)[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)=[O:14])[CH:9]=1)[CH3:2]>[Pd].CO>[CH2:55]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([NH:30][C:31](=[O:54])[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][OH:53])[CH:33]=2)=[C:8]([C:10]2[CH:11]=[C:12]([CH:27]=[CH:28][N:29]=2)[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)=[O:14])[CH:9]=1)[CH3:56]

Participants

4

Reactant 1

HCID 665882562-(5-(diethylamino)-2-(3-(1-hydroxy-3,6,9,12-tetraoxapentadec-14-yn-15-yl)benzamido)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

Product 1

HCID 696314862-(5-(diethylamino)-2-(3-(1-hydroxy-3,6,9,12-tetraoxapentadecan-15-yl)benzamido)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamideYield 841.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(5-(diethylamino)-2-(3-(1-hydroxy-3,6,9,12-tetraoxapentadec-14-yn-15-yl)benzamido)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide (107 mg, 0.014 mmol) and 10% palladium on carbon (water content 50%, 40 mg) in methanol (3 mL) was stirred under one atmosphere of H2 for 1 hour. The mixture was filtered and concentrated under vacuum to give the title compound (92 mg). 1H NMR (400 MHz, CDCl3, ppm) ε□12.13 (s, 1H), 8.81 (d, J=5.2 Hz, 1H), 8.39 J=9.0 Hz, 1H), 8.15 (s, 1H), 7.78 (d, J=7.7 Hz, 1H), 7.71 (s, 1H), 7.69 (dd, JAB=5.1 Hz, JAC=1.4 Hz, 1H), 7.64 (s, 1H), 7.63-7.54 (m, 3H), 7.47 (t, J=7.5 Hz, 1H), 7.37 (t, J=7.6 Hz, 1H), 7.32 (d, J=7.9 Hz, 1H), 6.95 (d, J=2.8 Hz, 1H), 7.67 (dd, JAB=9.0 Hz, JAC=2.3 Hz, 1H), 4.74 (d, J=6.1 Hz, 2H), 3.66-3.56 (m, 14H), 3.53-3.51 (m, 2H), 3.48 (t, J=6.5 Hz, 2H), 3.32 (quar, J=7.0 Hz, 4H), 2.96 (br s, 1H), 2.77 (t, J=7.2 Hz, 2H), 1.98-1.91 (m, 2H), 1.13 (t, J=6.9 Hz, 6H). MS (ES, m/z): 781.4 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1db7a8930d0a49c590d46ed019cd8801
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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