2-Chloro-3-nitropyridine → HCID 89726372, compound

HRID 1777732Notes

Reaction equation

HRID 1777732 reaction equation
[NH2:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].Cl.Cl[C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1.CCN(C(C)C)C(C)C>CC#N>[C:6]([O:5][C:3](=[O:4])[CH2:2][NH:1][C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 796132-Chloro-3-nitropyridineHCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 89726372HCID 89726372, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of H-Gly-OtBu.HCl (1.57 g) in MeCN (35 mL) was added 2-chloro-3-nitropyridine (1.5 g) and DIPEA (4.01 mL). The resulting yellow solution was heated up to 80° C. for 14 h. The reaction mixture was evaporated to dryness. The residue was taken up in DCM, washed with water and brine and the aq. phases were extracted with DCM. The combined org. layers were dried (MgSO4), filtrated off and evaporated in vacuo to afford 2.44 g of yellow solid. LC-MS (C): tR=0.81 min; [M+H]+: 254.27

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. washwashed with water and brine
  3. extractionthe aq. phases were extracted with DCM
  4. dry with materiallayers were dried (MgSO4)
  5. filtrationfiltrated off
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1b9ab608fe604cd1b06d4877f492a452
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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