Acrylic Acid → HCID 118116622, compound

HRID 1774650Notes

Reaction equation

HRID 1774650 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]([CH3:20])[C:6]1[N:11]=[C:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:8][CH:7]=1.[C:21](O)(=[O:24])[CH:22]=[CH2:23].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>[C:21]([NH:2][CH2:3][CH2:4][N:5]([CH3:20])[C:6]1[N:11]=[C:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:9]=[CH:8][CH:7]=1)(=[O:24])[CH:22]=[CH2:23]

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 118116348HCID 118116348, compound

Product 1

HCID 118116622HCID 118116622, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 110c (1.2 g, 4.5 mmol), acrylic acid (0.37 mL, 5.4 mmol), HATU (2.05 g, 5.4 mmol) and DIPEA (4.6 mL, 10.8 mmol) in DCM (30 mL) was stirred at rt overnight. The mixture was washed with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give tert-butyl 6-((2-acrylamidoethyl)(methyl)amino)pyridin-2-ylcarbamate 110d (1.2 g, 75%) as a brown oil. The material was used for the next step directly. ESI-LCMS: m/z=321.3

Workup

  1. washThe mixture was washed with water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cbd264cc061b40ddb754515b38e1c801
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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