Ethanolamine → 5-bromo-N-(2-hydroxyethyl)nicotinamide

HRID 58059Notes

Reaction equation

HRID 58059 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[NH2:11][CH2:12][CH2:13][OH:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O1CCOCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:11][CH2:12][CH2:13][OH:14])=[O:9]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 887075-Bromonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 237665285-bromo-N-(2-hydroxyethyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Bromonicotinic acid (0.020 g, 0.10 mmol), 2-aminoethanol (9.16 mg, 0.15 mmol), HATU (0.046 g, 0.12 mmol), DIPEA (0.052 g, 0.40 mmol), and dioxane (2 mL) were added to a 20 mL vial. The vial was sealed and placed on a heater/shaker for 3 days at 40° C. The reaction mixture, containing the title compound, was used without purification.

Workup

  1. customThe vial was sealed

Sources & evidence

ORD record
ord-3840cc9e65524acabad4942fd7de810b
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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