Diisopropylethylamine → HCID 58554133, compound

HRID 1631007Notes

Reaction equation

HRID 1631007 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[C:10]([O:14][C:15](=[O:18])[CH2:16][NH2:17])([CH3:13])([CH3:12])[CH3:11].CCN(C(C)C)C(C)C>CC(N(C)C)=O.CCOCC>[C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:17][CH2:16][C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:18])[CH:7]=1)#[N:9]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 151417Glycine tert-butyl esterHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 58554133HCID 58554133, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-chloro-4-cyanopyridine (1.00 g, 7.2 mmol), glycine tert-butyl ester (1.5 mL, 10.8 mmol) and DIEA (4.9 mL, 28.9 mmol) in anhydrous DMA (15 mL) was heated at 150° C. for 48 hours. The reaction mixture was diluted with Et2O (100 mL) and washed with water (2×50 mL) and brine (50 mL). The organic layer was dried (MgSO4) and the solvents were removed under reduced pressure. After purification by flash chromatography (silica, DCM), the title compound was obtained as a yellow oil. HPLC (Method A), Rt: 3.1 min (purity: 94%). UPLC/MS, M+(ESI): 178.0 ([M-tBu+2H]+), M−(ESI): 232.1. 1H NMR (DMSO-d6, 300 MHz) δ 8.15 (d, J=5.2 Hz, 1H), 7.44 (t, J=6.2 Hz, 1H), 6.93 (brs, 1H), 6.85 (dd, J=5.2, 1.3 Hz, 1H), 3.94 (d, J=6.2 Hz, 2H), 1.38 (s, 9H).

Workup

  1. washwashed with water (2×50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvents were removed under reduced pressure
  4. customAfter purification by flash chromatography (silica, DCM)

Sources & evidence

ORD record
ord-c8d0c065dbf34ee79092d69cf18c0313
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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