Diisopropylethylamine → HCID 58554194, compound

HRID 1631003Notes

Reaction equation

HRID 1631003 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.Cl.[C:11]([O:15][C:16](=[O:20])[CH2:17][CH2:18][NH2:19])([CH3:14])([CH3:13])[CH3:12].CCN(C(C)C)C(C)C>O1CCOCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:19][CH2:18][CH2:17][C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:20])=[N:3][CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 16218890Tert-butyl 3-aminopropanoate hydrochloride2×

Product 1

HCID 58554194HCID 58554194, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-chloronicotinonitrile (1.0 g, 7.2 mmol), beta-alanine tert-butyl ester hydrochloride (2.0 g, 11.0 mmol) and DIEA (4.9 mL, 28.9 mmol) in anhydrous dioxane (20 mL) was heated at reflux. After 24 hours, an additional amount of beta-alanine tert-butyl ester hydrochloride (0.5 g, 2.75 mmol) was added. After 24 additional hours at reflux, the reaction mixture was concentrated under reduced pressure. The residue was taken up with EtOAc (50 mL) and washed with water (2×20 mL) and brine (20 mL). The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. After precipitation from MTBE/pentane, the title compound was obtained as an off-white powder (1.28 g, 72%). HPLC (Method A), Rt: 2.7 min (purity: 99.9%). UPLC/MS, M+(ESI): 248.1, M−(ESI): 246.2. 1H NMR (DMSO-d6, 300 MHz) δ 8.40 (d, J=2.0 Hz, 1H), 7.67 (m, 2H), 6.56 (d, J=8.9 Hz, 1H), 3.50 (td, J=6.8, 6.0 Hz, 2H), 2.48 (t, J=6.8 Hz, 2H), 1.38 (s, 9H).

Workup

  1. temperatureat reflux
  2. temperatureAfter 24 additional hours at reflux
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. washwashed with water (2×20 mL) and brine (20 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customAfter precipitation from MTBE/pentane

Sources & evidence

ORD record
ord-2f4b00e63ef248baa40e0370c075c2e0
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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