Glycine tert-butyl ester → Tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate

HRID 1631011Notes

Reaction equation

HRID 1631011 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[Cl:10][C:11]1[C:12](Cl)=[N:13][CH:14]=[C:15]([CH:18]=1)[C:16]#[N:17]>>[Cl:10][C:11]1[C:12]([NH:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])=[N:13][CH:14]=[C:15]([C:16]#[N:17])[CH:18]=1

Participants

3

Reactant 2

HCID 151417Glycine tert-butyl esterHCID 128784645,6-Dichloropyridine-3-carbonitrile

Product 1

HCID 58554110Tert-butyl [(3-chloro-5-cyanopyridin-2-yl)amino]acetate

Procedure

A mixture of glycine tert-butyl ester (5.3 g, 40.4 mmol), TEA (5.6 mL, 40.4 mmol) and 5,6-dichloronicotinonitrile (Bionet GC-0755, 7.0 g, 40.4 mmol) was prepared and stirred at RT for 24 hours. The reaction mixture was filtered to remove inorganic solids and filtrate was concentrated under reduced pressure. The residue taken up with EtOAc (100 mL) and washed with water (2×100 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. After purification by flash chromatography (silica, pet ether/EtOAc), the title compound was obtained as a white powder. 1H NMR (DMSO-d6, 400 MHz) δ 8.41 (1H, d), 8.15 (1H, d), 7.84 (1H, t), 4.00 (2H, m), 1.38 (9H, s).

Workup

  1. customwas prepared
  2. filtrationThe reaction mixture was filtered
  3. customto remove inorganic solids and filtrate
  4. concentrationwas concentrated under reduced pressure
  5. washwashed with water (2×100 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customAfter purification by flash chromatography (silica, pet ether/EtOAc)

Sources & evidence

ORD record
ord-aedf92f5aac3451a867f51e4ad4d0dfb
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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