Pyridine → 4-(N'-(t-butoxycarbonyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(2-(ethoxycarbonyl)ethylcarbonyl)-N-(3-(6-((4-methoxybenzyl)oxy)-3-cyanophenyi)prop-2-en-1-yl)benzenamine

HRID 1700298Notes

Reaction equation

HRID 1700298 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH:23]=[CH:24][C:25]3[C:30]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)=[CH:29][CH:28]=[C:27]([C:41]#[N:42])[CH:26]=3)=[CH:17][C:16]=2[C:43]([F:46])([F:45])[F:44])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:48](=[O:56])[CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52].N1C=CC=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([C:48]([CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])=[O:56])[CH2:22][CH:23]=[CH:24][C:25]3[C:30]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)=[CH:29][CH:28]=[C:27]([C:41]#[N:42])[CH:26]=3)=[CH:17][C:16]=2[C:43]([F:46])([F:44])[F:45])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 701667714-(N (t-butoxycarbonyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(3-(6-((4-methoxybenzyl)oxy)-3-cyanophenyl)prop-2-en-1-yl)benzenamine

Product 1

HCID 867578004-(N'-(t-butoxycarbonyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(2-(ethoxycarbonyl)ethylcarbonyl)-N-(3-(6-((4-methoxybenzyl)oxy)-3-cyanophenyi)prop-2-en-1-yl)benzenamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-(N′-(t-butoxycarbonyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(3-(6-((4-methoxybenzyl)oxy)-3-cyanophenyl)prop-2-en-1-yl)benzenamine (1.39 g) in 20 mL of CH2Cl2 was added ethyl 4-chloro-4-oxobutyrate (0.43 g) and pyridine (1 mL) at 0° C. The resulting solution was allowed to warm to ambient temperature for 30 minutes and then diluted with 100 mL CH2Cl2. The organic layer was washed with saturated copper sulfate, dried and concentrated to afford 4-(N′-(t-butoxycarbonyl)piperidin-4-yl)oxy-3-trifluoromethyl-N-(2-(ethoxycarbonyl)ethylcarbonyl)-N-(3-(6-((4-methoxybenzyl)oxy)-3-cyanophenyi)prop-2-en-1-yl)benzenamine as a blue solid.

Workup

  1. washThe organic layer was washed with saturated copper sulfate
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d6eaae4473f94460aa5eed9bd80945f5
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

Loading…