Acrylic Acid → N-(2-(6-aminopyridin-2-ylamino)ethyl)acrylamide

HRID 1774636Notes

Reaction equation

HRID 1774636 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[N:7]=1.[C:13](O)(=[O:16])[CH:14]=[CH2:15].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>C(Cl)Cl>[NH2:12][C:8]1[N:7]=[C:6]([NH:5][CH2:4][CH2:3][NH:2][C:13](=[O:16])[CH:14]=[CH2:15])[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6581Acrylic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118117145N2-(2-aminoethyl)pyridine-2,6-diamine hydrochloride

Product 1

HCID 118116459N-(2-(6-aminopyridin-2-ylamino)ethyl)acrylamideYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 105c (1.88 g, 10 mmol), acrylic acid (720 mg, 10 mmol), HATU (3.80 g, 10 mmol) and DIPEA (6.97 mL, 40 mmol) in DCM (50 mL) was stirred at rt for 16 h. The reaction mixture was concentrated and the residue was purified by silica gel chromatography (EA/MeOH=4/1) to give N-(2-(6-aminopyridin-2-ylamino)ethyl)acrylamide 105d (1.07 g, 52%) as pale-yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel chromatography (EA/MeOH=4/1)

Sources & evidence

ORD record
ord-07bed91add7143f2a42c4d395ecea7d5
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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