Diisopropylethylamine → HCID 58554225, compound

HRID 1631005Notes

Reaction equation

HRID 1631005 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[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>CS(C)=O.CCOCC>[C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:19][CH2:18][CH2:17][C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:20])[CH:7]=1)#[N:9]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5686382-Chloro-4-cyanopyridineHCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

Product 1

HCID 58554225HCID 58554225, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-chloro-4-cyanopyridine (2.00 g, 14.4 mmol), beta-alanine tert-butyl ester hydrochloride (3.14 g, 17.3 mmol) and DIEA (9.88 mL, 57.7 mmol) in anhydrous DMSO (30 mL) was heated at 150° C. for 3 days. The reaction mixture was diluted with Et2O (100 mL) and washed with water (3×60 mL) and brine (60 mL). The organic layer was dried (MgSO4) and the solvents were removed under reduced pressure. Purification by flash chromatography (silica, EtOAc/cHex) gave the title compound as a brown oil. HPLC (Method A), Rt: 2.8 min (purity: 92.2%). UPLC/MS, M+(ESI): 248.1, M−(ESI): 246.2. 1H NMR (DMSO-d6, 300 MHz) δ 8.16 (dd, J=5.2, 0.7 Hz, 1H), 7.16 (t, J=5.7 Hz, 1H), 6.83 (m, 1H), 6.79 (dd, J=5.2, 1.4 Hz, 1H), 3.46 (td, J=6.8, 5.7 Hz, 2H), 2.46 (t, J=6.8 Hz, 2H), 1.38 (s, 9H).

Workup

  1. washwashed with water (3×60 mL) and brine (60 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvents were removed under reduced pressure
  4. customPurification by flash chromatography (silica, EtOAc/cHex)

Sources & evidence

ORD record
ord-d959ef62fe974dae8ada46bba02b9797
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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