Hydrochloric Acid → N-(4-((dimethylamino)methyl)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)acetamide, hydrochloride

HRID 576226Notes

Reaction equation

HRID 576226 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:40])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][C:23]([O:29]CC4C=CC(OC)=CC=4)=[C:24]([O:26][CH2:27][CH3:28])[CH:25]=3)=[CH:16][C:15]=2[F:39])=[CH:7][C:6]=1[C:41]([F:44])([F:43])[F:42])[CH3:3].[ClH:45]>C(Cl)Cl>[ClH:45].[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:40])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[C:24]([O:26][CH2:27][CH3:28])[C:23](=[O:29])[NH:22][CH:21]=3)=[CH:16][C:15]=2[F:39])=[CH:7][C:6]=1[C:41]([F:43])([F:42])[F:44])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90417302N-(4-((dimethylamino)methyl)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetamide

Product 1

HCID 90422983N-(4-((dimethylamino)methyl)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)acetamide, hydrochlorideYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of N-(4-((dimethylamino)methyl)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetamide (5.8 g, 7.30 mmol) in DCM (50 mL) was added HCl (1,4-dioxane, 5 mL, 20.00 mmol) at rt. The solution was stirred at 20° C. for 30 min. The solution was concentrated in vacuo to give the crude product. The crude material was purified by preparative HPLC (MeCN/H2O as eluants, acidic condition) to yield a off white solid of N-(4-((dimethylamino)methyl)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)acetamide, hydrochloride (1.5 g, 2.78 mmol, 38.1% yield). TLC (DCM/MeOH=5:1, Rf=0.3): 1H NMR (400 MHz, CD3OD) δ 8.21 (d, J=1.4 Hz, 1H), 8.04 (d, J=8.4 Hz, 1H), 7.75 (d, J=8.4 Hz, 1H), 7.36-7.53 (m, 5H), 4.50 (s, 2H), 4.20 (q, J=7.0 Hz, 2H), 3.87 (s, 2H), 2.95 (s, 6H), 1.50 (t, J=7.0 Hz, 3H); ES-LCMS m/z 492.2 (M+H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto give the crude product
  3. customThe crude material was purified by preparative HPLC (MeCN/H2O as eluants, acidic condition)

Sources & evidence

ORD record
ord-7f68b75ff6dd4fc4b04584ee2837df2d
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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