Acrylic Acid → HCID 118116322, compound

HRID 1774661Notes

Reaction equation

HRID 1774661 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:14]=[C:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:11][CH:10]=2)[CH2:4]1.[C:23](O)(=[O:26])[CH:24]=[CH2:25].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:23]([NH:2][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:14]=[C:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH:12]=[CH:11][CH:10]=2)[CH2:4]1)(=[O:26])[CH:24]=[CH2:25]

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 118116442HCID 118116442, compound

Product 1

HCID 118116322HCID 118116322, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 114c (1.39 g, 4.22 mmol), acrylic acid (0.3 mL, 4.5 mmol), HATU (1.7 g, 4.5 mmol) and DIPEA (3.8 mL, 9 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 (S)-tert-butyl 6-(3-acrylamidopiperidin-1-yl)pyridin-2-ylcarbamate 114d (880 mg, 60%) as brown oil. The material was used for the next step directly.

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-f202dd97d79e4cea826019a85c6688ee
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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