2-(Ethylamino)ethanol → 5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)nicotinamide

HRID 924033Notes

Reaction equation

HRID 924033 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH2:23]([NH:25][CH2:26][CH2:27][OH:28])[CH3:24]>>[Br:1][C:2]1[C:3]([N:25]([CH2:23][CH3:24])[CH2:26][CH2:27][OH:28])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8]

Participants

3

Reactant 2

HCID 80722-(Ethylamino)ethanolHCID 725460895-bromo-6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 899068415-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 33.1 using 5-bromo-6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)nicotinamide (Stage 169.2) and 2-ethylamino-ethanol to afford an off-white crystalline solid. (Reaction Time was 10 h). HPLC (Condition 4) tR=6.1 min, UPLC-MS (Condition 3) tR=1.21 min, m/z=466.2 [M+H]+.

Workup

  1. customto afford an off-white crystalline solid
  2. custom(Reaction Time was 10 h)

Sources & evidence

ORD record
ord-cfe930f677b241b89ed25581ac770930
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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