(E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acrylamide → (E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-(2-(dimethylamino)ethoxy)phenyl)butyl)acrylamide

HRID 2406585Notes

Reaction equation

HRID 2406585 reaction equation
[Br:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:9](\[C:31]#[N:32])/[C:10]([NH:12][CH:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]([CH2:29]C)[CH2:27]C)=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[O:11])[CH:5]=[CH:4][CH:3]=1.C(CC(NC(C1C=CC(OCCN(C)C)=CC=1)CCC)=O)#N>>[Br:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:9](\[C:31]#[N:32])/[C:10]([NH:12][CH:13]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH2:25][N:26]([CH3:27])[CH3:29])=[CH:21][CH:22]=2)[CH2:14][CH2:15][CH3:16])=[O:11])[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 56947930(E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acrylamideHCID 668219482-Cyano-N-(1-(4-(2-(dimethylamino)ethoxy)phenyl)butyl)acetamide

Product 1

HCID 87168238(E)-3-(6-Bromopyridin-2-yl)-2-cyano-N-(1-(4-(2-(dimethylamino)ethoxy)phenyl)butyl)acrylamide

Procedure

The title compound was prepared by using a similar procedure as described for the preparation of 33 except that 2-cyano-N-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-butyl)acetamide (30) was used instead of 2-cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acetamide (29). This produced the crude product which was purified by flash silica gel column chromatography, eluting with 4:96 methanol/dichloromethane, to give 35 (120 mg, 76%) as a yellow oil: MS (ES+) m/z 471.1 (M+H)+.

Workup

  1. customThis produced the crude product which

Sources & evidence

ORD record
ord-c88e0fccbdaf434198c0e48e17ad0464
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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